Transformación de Monoterpenos en Productos de Valor Agregado mediante Reacciones One-pot

Procesos ambientalmente amigables y sostenibles (minimización o poco uso de solventes tóxicos así como la no generación de residuos) han sido uno de los ejes fundamentales desde la perspectiva de la química verde ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1016/j.jsps.2018.07.011","ISSN":"13190164","abstract":"The growing process of industrialization was a milestone for world economic evolution. Since the 1940s, social movements have revolutionized green chemistry and provided shifts in industrial positions and sustainable processes with advances in environmental impact and awareness of companies and population. Paul Anastas and John Warner, in the 1990s, postulated the 12 principles of Green Chemistry, which are based on the minimization or non-use of toxic solvents in chemical processes and analyzes, as well as, the non-generation of residues from these processes. One of the most active areas of Research and Development in Green Chemistry is the development of analytical methodologies, giving rise to the so-called Green Analytical Chemistry. The impacts of green chemistry on pharmaceutical analyzes, environmental, population, analyst and company are described in this review and they are multidimensional. Every choice and analytical attitude has consequences both in the final product and in everything that surrounds it. The future of green chemistry as well as our future and the environment is also contemplated in this work.","author":[{"dropping-particle":"","family":"Marco","given":"Bianca Aparecida","non-dropping-particle":"de","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Rechelo","given":"Bárbara Saú","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Tótoli","given":"Eliane Gandolpho","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Kogawa","given":"Ana Carolina","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Salgado","given":"Hérida Regina Nunes","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Saudi Pharmaceutical Journal","id":"ITEM-1","issue":"1","issued":{"date-parts":[["2019"]]},"page":"1-8","publisher":"King Saud University","title":"Evolution of green chemistry and its multidimensional impacts: A review","type":"article-journal","volume":"27"},"uris":["http://www.mendeley.com/documents/?uuid=18b67783-d1ca-4fc4-837b-aebe10b13964"]}],"mendeley":{"formattedCitation":"[1]","plainTextFormattedCitation":"[1]","previouslyFormattedCitation":"[1]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[1]ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1021/cr078380v","ISSN":"00092665","PMID":"17564478","author":[{"dropping-particle":"","family":"Horváth","given":"István T.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Anastas","given":"Paul T.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Chemical Reviews","id":"ITEM-1","issue":"6","issued":{"date-parts":[["2007"]]},"page":"2169-2173","title":"Innovations and green chemistry","type":"article-journal","volume":"107"},"uris":["http://www.mendeley.com/documents/?uuid=2adec42e-a8a2-4476-be2d-34b4690a47ea"]}],"mendeley":{"formattedCitation":"[2]","plainTextFormattedCitation":"[2]","previouslyFormattedCitation":"[2]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[2]. Dichos procesos han sido empleados en la obtención de compuestos de valor agregado con alta aplicación industrial usando monoterpenos extraídos directamente de aceites esenciales e inspirados en la biomasa, como el α-pineno, β-pineno y limoneno (Figura 1) ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1021/cr500407m","ISBN":"1520-6890 (Electronic)\\r0009-2665 (Linking)","ISSN":"15206890","PMID":"25906177","author":[{"dropping-particle":"","family":"Golets","given":"Mikhail","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Ajaikumar","given":"Samikannu","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Mikkola","given":"Jyri Pekka","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Chemical Reviews","id":"ITEM-1","issue":"9","issued":{"date-parts":[["2015"]]},"page":"3141-3169","title":"Catalytic Upgrading of Extractives to Chemicals: Monoterpenes to \"eXICALS\"","type":"article-journal","volume":"115"},"uris":["http://www.mendeley.com/documents/?uuid=e343d0aa-7ae1-4fe9-9736-8deb2f9e608f"]}],"mendeley":{"formattedCitation":"[3]","plainTextFormattedCitation":"[3]","previouslyFormattedCitation":"[3]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[3]. Sin embargo, en muchos casos la síntesis de tales productos requiere etapas secuenciales, uso de solventes poco benignos y numerosas etapas de purificación, a lo cual se suma los bajos rendimientos, así como cantidades indeseadas de productos secundarios (por ejemplo, por 1 kg de producto farmacéutico activo se generan 25-100 kg de productos indeseados) ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1039/c4ra13506g","ISSN":"20462069","abstract":"Incompatible organic reactions impede efficient green synthesis by making multi-component or cascade reactions a big challenge. This review highlights pot-in-pot reactions (multiple reactions carried out in one pot by separating key reactions with a thin polymeric membrane) as an efficient, green synthetic alternative to conventional synthesis. We discuss the advantages of homogeneous processes to develop new cascade reaction sequences by reviewing the use of polymeric thimbles as selective semi-permeable walls. These thimbles allow small organic molecules to diffuse through while retaining polar reagents, polar solvents, and/or organometallic catalysts. The dynamic and versatile nature of this technique is demonstrated by performing 2- and 3-step cascade reactions in one glass pot. A pot-in-pot reaction approach to synthesis circumvents the need to isolate intermediates, or handling of toxic/unpleasant by-products, therefore enabling synthesis of otherwise challenging molecules, improving the efficiency, or enabling greener approaches to modular synthesis.","author":[{"dropping-particle":"","family":"Atkinson","given":"M. B.J.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Oyola-Reynoso","given":"S.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Luna","given":"R. E.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Bwambok","given":"D. K.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Thuo","given":"M. M.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"RSC Advances","id":"ITEM-1","issue":"1","issued":{"date-parts":[["2015"]]},"page":"597-607","title":"Pot-in-pot reactions: A simple and green approach to efficient organic synthesis","type":"article-journal","volume":"5"},"uris":["http://www.mendeley.com/documents/?uuid=b5d8a6a1-d60e-4a5f-a8de-bc57117c1e30"]}],"mendeley":{"formattedCitation":"[4]","plainTextFormattedCitation":"[4]","previouslyFormattedCitation":"[4]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[4], haciendo estos procesos poco factibles técnica y económicamente. Una solución a este planteamiento ha sido la creación de reacciones one-pot (tandem, cascada) que, además, pueden mejorar la eficiencia atómica con bajo factor E (kg subproducto/kg producto puro), disminución de etapas con minimización de requerimientos energéticos e intensificación de procesos ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1021/cr1002084","ISSN":"00092665","author":[{"dropping-particle":"","family":"Climent","given":"Maria J.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Corma","given":"Avelino","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Iborra","given":"Sara","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Chemical Reviews","id":"ITEM-1","issue":"2","issued":{"date-parts":[["2011"]]},"page":"1072-1133","title":"Heterogeneous catalysts for the one-pot synthesis of chemicals and fine chemicals","type":"article-journal","volume":"111"},"uris":["http://www.mendeley.com/documents/?uuid=40120f3c-0734-48ff-859c-79610b163a35"]}],"mendeley":{"formattedCitation":"[5]","plainTextFormattedCitation":"[5]","previouslyFormattedCitation":"[5]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[5]. Lo anterior se debe principalmente a que en las denominadas reacciones one-pot tiene lugar una simplicidad operacional al haber una reducción del número de etapas de purificación, por lo que hay una disminución efectiva de los residuos generados y una disminución del tiempo de síntesis ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1016/j.tetlet.2010.10.108","ISSN":"00404039","abstract":"A novel tandem one-pot method for the synthesis of α-aminomethylene- γ-butyrolactone derivatives has been developed through the regioselective epoxide opening reactions with the Blaise reaction intermediates, generated by the reaction of a Reformatsky reagent with nitriles. Formation of a modified Blaise reaction intermediate by the addition of a stoichiometric amount of n-BuLi followed by slow addition of epoxide is required for the good yield of γ-butyrolactones. © 2010 Elsevier Ltd. All rights reserved.","author":[{"dropping-particle":"","family":"Ko","given":"Young Ok","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Chun","given":"Yu Sung","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Kim","given":"Youngmee","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Kim","given":"Sung Jin","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Shin","given":"Hyunik","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Lee","given":"Sang Gi","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Tetrahedron Letters","id":"ITEM-1","issue":"52","issued":{"date-parts":[["2010"]]},"page":"6893-6896","publisher":"Elsevier Ltd","title":"Tandem one-pot synthesis of α-(aminomethylene)-γ-butyrolactones via regioselective epoxide ring-opening with the Blaise reaction intermediate","type":"article-journal","volume":"51"},"uris":["http://www.mendeley.com/documents/?uuid=576eabc0-ddad-4446-a1bc-0bbb102db551"]},{"id":"ITEM-2","itemData":{"DOI":"10.1039/c4ra13506g","ISSN":"20462069","abstract":"Incompatible organic reactions impede efficient green synthesis by making multi-component or cascade reactions a big challenge. This review highlights pot-in-pot reactions (multiple reactions carried out in one pot by separating key reactions with a thin polymeric membrane) as an efficient, green synthetic alternative to conventional synthesis. We discuss the advantages of homogeneous processes to develop new cascade reaction sequences by reviewing the use of polymeric thimbles as selective semi-permeable walls. These thimbles allow small organic molecules to diffuse through while retaining polar reagents, polar solvents, and/or organometallic catalysts. The dynamic and versatile nature of this technique is demonstrated by performing 2- and 3-step cascade reactions in one glass pot. A pot-in-pot reaction approach to synthesis circumvents the need to isolate intermediates, or handling of toxic/unpleasant by-products, therefore enabling synthesis of otherwise challenging molecules, improving the efficiency, or enabling greener approaches to modular synthesis.","author":[{"dropping-particle":"","family":"Atkinson","given":"M. B.J.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Oyola-Reynoso","given":"S.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Luna","given":"R. E.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Bwambok","given":"D. K.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Thuo","given":"M. M.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"RSC Advances","id":"ITEM-2","issue":"1","issued":{"date-parts":[["2015"]]},"page":"597-607","title":"Pot-in-pot reactions: A simple and green approach to efficient organic synthesis","type":"article-journal","volume":"5"},"uris":["http://www.mendeley.com/documents/?uuid=b5d8a6a1-d60e-4a5f-a8de-bc57117c1e30"]},{"id":"ITEM-3","itemData":{"DOI":"10.1021/cr1002084","ISSN":"00092665","author":[{"dropping-particle":"","family":"Climent","given":"Maria J.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Corma","given":"Avelino","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Iborra","given":"Sara","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Chemical Reviews","id":"ITEM-3","issue":"2","issued":{"date-parts":[["2011"]]},"page":"1072-1133","title":"Heterogeneous catalysts for the one-pot synthesis of chemicals and fine chemicals","type":"article-journal","volume":"111"},"uris":["http://www.mendeley.com/documents/?uuid=40120f3c-0734-48ff-859c-79610b163a35"]}],"mendeley":{"formattedCitation":"[4–6]","plainTextFormattedCitation":"[4–6]","previouslyFormattedCitation":"[4–6]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[4–6]. Figura 1. Estructura química del α-pineno, β-pineno y limoneno. La transformación de monoterpenos y sus derivados es de gran interés en la industria química y farmacéutica ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1515/pac-2017-0109","ISSN":"13653075","abstract":"Monoterpenes and their derivatives play an important role in the creation of new biologically active compounds including drugs. The review focuses on the data on various types of biological activity exhibited by monoterpenes and their derivatives, including analgesic, anti-inflammatory, anticonvulsant, antidepressant, anti-Alzheimer, anti-Parkinsonian, antiviral, and antibacterial (anti-tuberculosis) effects. Searching for novel potential drugs among monoterpene derivatives shows great promise for treating various pathologies. Special attention is paid to the effect of absolute configuration of monoterpenes and monoterpenoids on their activity.","author":[{"dropping-particle":"","family":"Salakhutdinov","given":"Nariman F.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Volcho","given":"Konstantin P.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Yarovaya","given":"Olga I.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Pure and Applied Chemistry","id":"ITEM-1","issue":"8","issued":{"date-parts":[["2017"]]},"page":"1105-1117","title":"Monoterpenes as a renewable source of biologically active compounds","type":"article-journal","volume":"89"},"uris":["http://www.mendeley.com/documents/?uuid=08992f2c-092d-4bbd-a3c6-848f3e3f4e38"]},{"id":"ITEM-2","itemData":{"DOI":"10.1016/j.cbpa.2016.06.002","ISBN":"1879-0402 (Electronic)\\r1367-5931 (Linking)","ISSN":"18790402","PMID":"27315341","abstract":"Synthetic biology is opening up new opportunities for the sustainable and efficient production of valuable chemicals in engineered microbial factories. Here we review the application of synthetic biology approaches to the engineering of monoterpene/monoterpenoid production, highlighting the discovery of novel catalytic building blocks, their accelerated assembly into functional pathways, general strategies for product diversification, and new methods for the optimization of productivity to economically viable levels. Together, these emerging tools allow the rapid creation of microbial production systems for a wide range of monoterpenes and their derivatives for a diversity of industrial applications.","author":[{"dropping-particle":"","family":"Zebec","given":"Ziga","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Wilkes","given":"Jonathan","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Jervis","given":"Adrian J.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Scrutton","given":"Nigel S.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Takano","given":"Eriko","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Breitling","given":"Rainer","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Current Opinion in Chemical Biology","id":"ITEM-2","issued":{"date-parts":[["2016"]]},"page":"37-43","publisher":"The Author(s)","title":"Towards synthesis of monoterpenes and derivatives using synthetic biology","type":"article-journal","volume":"34"},"uris":["http://www.mendeley.com/documents/?uuid=c55668f2-a6a1-4b0a-95f4-badc1024f286"]},{"id":"ITEM-3","itemData":{"DOI":"10.1023/B:TOCA.0000013549.60930.da","ISBN":"10225528","ISSN":"10225528","abstract":"A review covering some of the key catalytic transformations of the major monoterpene feedstocks. Monoterpenes are key ingredients in the flavor and fragrance industry, with a- and ß-pinene (obtained from turpentine) being some of the most important. The review focuses on the hydrocarbons; pinene, limonene, carene, and the interconversion of the monooxygenates; geraniol/nerol, citronellol, citral, and citronellal. The major areas covered are catalytic hydrogenation/hydrogenolysis, dehydrogenation, rearrangement/isomerization/aromatization, reactions with carbon monoxide, epoxidation, and the addition of alcohols and acids.","author":[{"dropping-particle":"","family":"Swift","given":"Karl A.D.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Topics in Catalysis","id":"ITEM-3","issue":"1-4","issued":{"date-parts":[["2004"]]},"page":"143-155","title":"Catalytic transformations of the major terpene feedstocks","type":"article-journal","volume":"27"},"uris":["http://www.mendeley.com/documents/?uuid=1d80a2e0-51b4-4623-bbfc-a1a4263e549d"]},{"id":"ITEM-4","itemData":{"DOI":"10.1002/9783527612390","ISBN":"9783527612390","ISSN":"0300-3930","PMID":"1514462727","abstract":"Common Fragrance and Flavor Materials, by K. As such, I found this book well succeeds in its BAUER, D. GARBE and H. SURBURY, Third Edition, objectives. The first half of the book deals with single Wiley, VCH, Weinheim, 1997. 278 pp. £60. ISBN 3-fragrance components, which are gathered together 517-28850-3. according to their chemical structures from aliphatics and terpenoids, through cycloaliphatics, and aro-Not having consulted the two earlier editions, I cannot matics to phenolics and heterocyclic derivatives. By comment directly on the revisions that have taken contrast, the second half lists the constituents of the place for this third edition. However, the authors natural raw materials of the flavour and fragrance assure the readers that many improvements have industry in alphabetical order from allium oils to taken place. In particular, references have been added ylang-ylang oil. Some practical details of oil isolation to the second half of the book, allowing newcomers and notes on fragrance classification are also included. to find an original literature report for all essential At the end there is a list of CAS registry numbers, as oils listed. Some readers may be disappointed that well as a general index and 45 references. All phyto-some aspects of fragrance materials have not been chemicals working with the volatiles of plants will find covered extensively (e.g. floral fragrance constituents) this a useful compendium to have on their book-but the authors do clearly state that this book is shelves. expressly aimed at the general reader rather than the Studies in Natural Products Chemistry, edited by is so often lacking from this type of account. The use ATTA-UR-RAHMAN, vol. 19, Structure and Chemistry of aliphatic nitro compounds for the construction of (part E), 1997, viii + 850, Elsevier, $509.50. natural products is especially welcome, since this topic has not been covered for 20 years. Methodology also The first volume of this series appeared less than ten features prominently in a chapter on the synthesis years ago (in 1988), and the series has always fulfilled of marine haloethers, and the discussion of enzyme-its aims of providing timely reviews of all aspects of mediated biomimetic syntheses will be of considerable natural products' chemistry. It must be said at the contemporary interest. The account of synthetic outset, that the price of the more recent volumes has approaches to the newly discovered glycosidase taken them quite beyond …","author":[{"dropping-particle":"","family":"Breitmaier","given":"Eberhard","non-dropping-particle":"","parse-names":false,"suffix":""}],"id":"ITEM-4","issued":{"date-parts":[["1997"]]},"title":"Common Fragrance and Flavor Materials","type":"book"},"uris":["http://www.mendeley.com/documents/?uuid=62b0a6af-72ec-4382-91f3-cf31b85ca381"]}],"mendeley":{"formattedCitation":"[7–10]","plainTextFormattedCitation":"[7–10]","previouslyFormattedCitation":"[7–10]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[7–10]. Por ejemplo, el α-pineno puede ser epoxidado e isomerizado en aldehído canfolénico cuyo interés y aplicación está relacionado con la industria de las fragancias y como antiséptico, además que muchos de sus isómeros presenta propiedades excepcionales en química medicinal como potentes componente activos contra el cáncer ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1039/C8CY01231H","ISSN":"2044-4753","abstract":"Campholenic aldehyde is a highly valuable fine chemical that can be obtained by multistep synthesis from monoterpene α-pinene isolated from turpentine oil.","author":[{"dropping-particle":"","family":"Pitínová-Štekrová","given":"Martina","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Eliášová","given":"Pavla","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Weissenberger","given":"Tobias","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Shamzhy","given":"Mariya","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Musilová","given":"Zuzana","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Čejka","given":"Jiří","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Catalysis Science & Technology","id":"ITEM-1","issue":"18","issued":{"date-parts":[["2018"]]},"page":"4690-4701","title":"Highly selective synthesis of campholenic aldehyde over Ti-MWW catalysts by α-pinene oxide isomerization","type":"article-journal","volume":"8"},"uris":["http://www.mendeley.com/documents/?uuid=7dd6f216-06de-4039-9e06-c73a6c00c7fb"]},{"id":"ITEM-2","itemData":{"DOI":"10.1016/j.apcata.2019.04.029","ISSN":"0926860X","abstract":"Fe and Cu based heterogeneous catalysts were evaluated in the isomerization reaction of α- and β-pinene epoxides. The metals were incorporated on SBA-15 and MCM-41 using incipient wetness impregnation procedure and the materials were characterized by XRD, Raman spectroscopy, BET analysis, NH 3 -TPD, TEM and XPS. 1.4/Fe-MCM-41 was the catalyst with the highest TON value (364) and α-pinene epoxide conversion (73%) with a campholenic aldehyde selectivity of 59%, while from β-pinene epoxide 1.4/Fe-SBA-15 was the material with the highest TON (299) and selectivity (100%) to myrtanal with a substrate conversion of 60%. Cu based materials presented lowest TON value for the rearrangement of β-pinene epoxide than using α-pinene epoxide as substrate. Besides, it was elucidated that the formation of campholenic aldehyde and myrtanal is function of the presence of metal oxides, mean particle diameter and the strength of acidity; moreover, the most active catalysts did not present leaching under the reaction conditions. 1.4/Fe-MCM-41 can be used until five times without loss of catalytic activity with α pinene epoxide. Based on the characterization and different products synthetized, a reaction mechanism for the rearrangement reaction of α-pinene epoxide is proposed. This is the first report of Cu heterogenized on mesoporous materials for the isomerization reaction of monoterpenes epoxides.","author":[{"dropping-particle":"","family":"Sánchez-Velandia","given":"Julián E.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Villa","given":"Aída Luz","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Applied Catalysis A: General","id":"ITEM-2","issued":{"date-parts":[["2019"]]},"title":"Isomerization of α- and β- pinene epoxides over Fe or Cu supported MCM-41 and SBA-15 materials","type":"article-journal"},"uris":["http://www.mendeley.com/documents/?uuid=1fde1811-6e8b-3cbc-bdc3-7b4ffb38e549"]},{"id":"ITEM-3","itemData":{"author":[{"dropping-particle":"","family":"Frater","given":"G.;BajgrowiczJ.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"European patent application.","id":"ITEM-3","issue":"12","issued":{"date-parts":[["1998"]]},"title":"Optical isomers of derivatives of campholenic aldehyde","type":"article-journal"},"uris":["http://www.mendeley.com/documents/?uuid=c014b6b0-23f6-461a-bc06-ee41d611aab1"]},{"id":"ITEM-4","itemData":{"DOI":"10.1016/j.apcatb.2006.01.021","author":[{"dropping-particle":"","family":"Medina","given":"F","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Tichit","given":"D","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Pe","given":"J","non-dropping-particle":"","parse-names":false,"suffix":""}],"id":"ITEM-4","issued":{"date-parts":[["2007"]]},"page":"577-584","title":"Aldol condensation of campholenic aldehyde and MEK over activated hydrotalcites","type":"article-journal","volume":"70"},"uris":["http://www.mendeley.com/documents/?uuid=2db1425e-9a5b-4db3-9022-c295492492b7"]}],"mendeley":{"formattedCitation":"[11–14]","plainTextFormattedCitation":"[11–14]","previouslyFormattedCitation":"[11–14]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[11–14]. Este aldehído, a su vez, mediante reacciones de condensación aldólica puede ser convertido en una serie de homólogos de la fragancia de sándalo (polisantol ®) cuya aplicación económica es atractiva ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1002/hlca.19920750507","ISSN":"15222675","abstract":"In connection with structure‐activity relationship studies, analogues of campholenal ((+)‐4b), an important building block for sandalwood‐like odorants, were prepared. The five‐membered‐ring analogues 4 were obtained by epoxidation of the corresponding α‐pinene derivatives 2, followed by catalytic ZnBr2 isomerisation (Scheme 2). The six‐membered‐ring skeleton was obtained by ozonolysis of α‐campholenyl acetate ((−)‐14b), followed by intramolecular aldol condensation (Scheme 5). 13C‐NMR assignments are given. Copyright © 1992 Verlag GmbH & Co. KGaA, Weinheim","author":[{"dropping-particle":"","family":"Chapuis","given":"Christian","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Brauchli","given":"Robert","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Helvetica Chimica Acta","id":"ITEM-1","issue":"5","issued":{"date-parts":[["1992"]]},"page":"1527-1546","title":"Preparation of Campholenal Analogues: Chirons for the lipophilic moiety of sandalwood‐like odorant alcohols","type":"article-journal","volume":"75"},"uris":["http://www.mendeley.com/documents/?uuid=c329db7f-8c0f-4d49-8c4b-d0928542cd35"]},{"id":"ITEM-2","itemData":{"DOI":"10.1016/j.apcata.2013.10.044","ISBN":"0926-860X","ISSN":"0926860X","abstract":"α-Pinene oxide, an oxygenated derivative of α-pinene, can be converted into various valuable substances useful as flavour, fragrance and pharmaceutical compounds. Campholenic aldehyde is one of the most desired products of α-pinene oxide isomerization being a valuable intermediate for the production of sandalwood-like fragrances. Iron modified zeolites Beta-75 and ZSM-5, mesoporous material MCM-41, silica and alumina were prepared by two methods (impregnation and solid-state ion exchange) and tested for selective preparation of campholenic aldehyde by isomerization of α-pinene oxide. The characterization of tested catalyst was carried out using scanning electron microscope analysis, nitrogen adsorption measurements, pyridine adsorption-desorption with FTIR, X-ray absorption spectroscopy measurements, XPS-analysis, 29Si MAS NMR and 27Al MAS NMR and X-ray diffraction. The isomerization of α-pinene oxide was carried out in toluene as a solvent at 70 C. The main properties influencing the activity and the selectivity are the acidic and structural properties of the tested catalysts. The highest selectivity of 66% was achieved at complete conversion of α-pinene oxide with Fe-MCM-41. © 2013 Elsevier Ltd. All rights reserved.","author":[{"dropping-particle":"","family":"Stekrova","given":"Martina","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Kumar","given":"Narendra","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Aho","given":"Atte","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Sinev","given":"Ilia","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Grünert","given":"Wolfgang","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Dahl","given":"Johnny","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Roine","given":"Jorma","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Arzumanov","given":"Sergey S.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Mäki-Arvela","given":"Päivi","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Murzin","given":"Dmitry Yu","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Applied Catalysis A: General","id":"ITEM-2","issued":{"date-parts":[["2014"]]},"page":"162-176","publisher":"Elsevier B.V.","title":"Isomerization of α-pinene oxide using Fe-supported catalysts: Selective synthesis of campholenic aldehyde","type":"article-journal","volume":"470"},"uris":["http://www.mendeley.com/documents/?uuid=e904b687-4596-4607-acdf-723bd48e07cb"]}],"mendeley":{"formattedCitation":"[15,16]","plainTextFormattedCitation":"[15,16]","previouslyFormattedCitation":"[15,16]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[15,16]. Por otro lado, el β-pineno, que puede ser extraído de aceites de trementina (Pinus Caribaeae, P. palustris, P. pinaster) y de la producción de la celulosa (sulfate turpertine) ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1002/9783527612390","ISBN":"9783527612390","ISSN":"0300-3930","PMID":"1514462727","abstract":"Common Fragrance and Flavor Materials, by K. As such, I found this book well succeeds in its BAUER, D. GARBE and H. SURBURY, Third Edition, objectives. The first half of the book deals with single Wiley, VCH, Weinheim, 1997. 278 pp. £60. ISBN 3-fragrance components, which are gathered together 517-28850-3. according to their chemical structures from aliphatics and terpenoids, through cycloaliphatics, and aro-Not having consulted the two earlier editions, I cannot matics to phenolics and heterocyclic derivatives. By comment directly on the revisions that have taken contrast, the second half lists the constituents of the place for this third edition. However, the authors natural raw materials of the flavour and fragrance assure the readers that many improvements have industry in alphabetical order from allium oils to taken place. In particular, references have been added ylang-ylang oil. Some practical details of oil isolation to the second half of the book, allowing newcomers and notes on fragrance classification are also included. to find an original literature report for all essential At the end there is a list of CAS registry numbers, as oils listed. Some readers may be disappointed that well as a general index and 45 references. All phyto-some aspects of fragrance materials have not been chemicals working with the volatiles of plants will find covered extensively (e.g. floral fragrance constituents) this a useful compendium to have on their book-but the authors do clearly state that this book is shelves. expressly aimed at the general reader rather than the Studies in Natural Products Chemistry, edited by is so often lacking from this type of account. The use ATTA-UR-RAHMAN, vol. 19, Structure and Chemistry of aliphatic nitro compounds for the construction of (part E), 1997, viii + 850, Elsevier, $509.50. natural products is especially welcome, since this topic has not been covered for 20 years. Methodology also The first volume of this series appeared less than ten features prominently in a chapter on the synthesis years ago (in 1988), and the series has always fulfilled of marine haloethers, and the discussion of enzyme-its aims of providing timely reviews of all aspects of mediated biomimetic syntheses will be of considerable natural products' chemistry. It must be said at the contemporary interest. The account of synthetic outset, that the price of the more recent volumes has approaches to the newly discovered glycosidase taken them quite beyond …","author":[{"dropping-particle":"","family":"Breitmaier","given":"Eberhard","non-dropping-particle":"","parse-names":false,"suffix":""}],"id":"ITEM-1","issued":{"date-parts":[["1997"]]},"title":"Common Fragrance and Flavor Materials","type":"book"},"uris":["http://www.mendeley.com/documents/?uuid=62b0a6af-72ec-4382-91f3-cf31b85ca381"]}],"mendeley":{"formattedCitation":"[10]","plainTextFormattedCitation":"[10]","previouslyFormattedCitation":"[10]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[10] puede ser epoxidado ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1016/j.apcata.2004.04.005","ISSN":"0926860X","abstract":"The present work describes a novel oxidation of β-pinene, with either dioxygen or hydrogen peroxide, over heterogeneous catalysts based on magnetite doped with Co or Mn, of general formula Fe3-xMxO4(M=Mn, Co; x=0-0.75) under solvent free conditions. In this process, β-pinene is converted to the products valuable for perfume and flavor industries, i.e. pinocarveol, pinocarvone, myrtenol and myrtenal, in excellent selectivity of up to 95%. The total concentration of these derivatives in the final mixture reaches 25-30wt.%. The catalysts undergo no metal leaching and can be easily recovered either magnetically or by filtration and reused several times. © 2004 Elsevier B.V. All rights reserved.","author":[{"dropping-particle":"","family":"Menini","given":"Luciano","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Silva","given":"Márcio J.","non-dropping-particle":"Da","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Lelis","given":"Maria F.F.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Fabris","given":"José D.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Lago","given":"Rochel M.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"V.","family":"Gusevskaya","given":"Elena","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Applied Catalysis A: General","id":"ITEM-1","issue":"1-2","issued":{"date-parts":[["2004"]]},"page":"117-121","title":"Novel solvent free liquid-phase oxidation of β-pinene over heterogeneous catalysts based on Fe3-xMxO4(M=Co and Mn)","type":"article-journal","volume":"269"},"uris":["http://www.mendeley.com/documents/?uuid=344cc6e3-1bc5-49a8-9b18-75e81b45db95"]},{"id":"ITEM-2","itemData":{"DOI":"10.1134/S1070363217080059","ISSN":"1070-3632","author":[{"dropping-particle":"V.","family":"Fomenko","given":"V.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"V.","family":"Bakhvalov","given":"O.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Kollegov","given":"V. F.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Salakhutdinov","given":"N. F.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Russian Journal of General Chemistry","id":"ITEM-2","issue":"8","issued":{"date-parts":[["2017"]]},"page":"1675-1679","title":"Catalytic epoxidation of β-pinene with aqueous hydrogen peroxide","type":"article-journal","volume":"87"},"uris":["http://www.mendeley.com/documents/?uuid=c920a355-b415-47e5-89f8-33477fe436c4"]}],"mendeley":{"formattedCitation":"[17,18]","plainTextFormattedCitation":"[17,18]","previouslyFormattedCitation":"[17,18]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[17,18] e isomerizado en alcoholes alílicos y compuestos carbonílicos, como mirtanal, mirtenol y alcohol perílico, los cuales son potenciales para su uso directo en química farmacéutica ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1016/j.cattod.2014.05.024","ISBN":"09205861","ISSN":"09205861","abstract":"The isomerisation of β-pinene oxide was studied over supported ionic liquid catalysts (SILCAs) consisting of Lewis acids in immobilized ionic liquid. SILCAs were demonstrated as efficient catalysts for the transformation of β-pinene oxide to myrtanal with the product distribution and activity being dependent on the nature of the ionic liquid and Lewis acid strength of catalytic species. With the catalyst ZnCl2/[N(3-OH-Pr)Py][NTf2]/ACC, the highest myrtanal molar yield obtained was 68%.","author":[{"dropping-particle":"","family":"Salminen","given":"Eero","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Rujana","given":"Luis","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Mäki-Arvela","given":"Päivi","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Virtanen","given":"Pasi","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Salmi","given":"Tapio","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Mikkola","given":"Jyri Pekka","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Catalysis Today","id":"ITEM-1","issue":"P2","issued":{"date-parts":[["2015"]]},"page":"318-321","publisher":"Elsevier B.V.","title":"Biomass to value added chemicals: Isomerisation of β-pinene oxide over supported ionic liquid catalysts (SILCAs) containing Lewis acids","type":"article-journal","volume":"257"},"uris":["http://www.mendeley.com/documents/?uuid=6e26e842-5cf5-4bfa-a550-93959bded8ca"]},{"id":"ITEM-2","itemData":{"DOI":"10.1016/j.apcata.2010.03.056","ISBN":"0926-860X","ISSN":"0926860X","abstract":"The epoxide rearrangement of β-pinene oxide into myrtanal was studied in the presence of solid Lewisacid catalysts. Different metals such as Zr, Sn, Ti, Nb, Ta, Al, and Ga have been incorporated within network positions of zeolite Beta by isomorphous substitution. The materials have been characterized by powdered X-ray diffraction (XRD), IR spectroscopy and by in situ IR spectroscopy on adsorbed molecules (cyclohexanone and pyridine). Among the studied catalysts Zr-Beta gave the best selectivity (up to 94%) in acetonitrile as solvent at practically complete conversion. In this epoxide rearrangement the solvent has to be selected to balance the competitive adsorption of the product. Product desorption is enhanced with acetonitrile which results in a selectivity increase with only a small penalty on the rate of reaction. Zr-Beta has been reused in the batch mode and in a fixed-bed reactor for several times and analysis of the reused catalyst indicated that Zr-Beta is a robust catalyst for the epoxide rearrangement. Leaching of the metal or crystal degradation has not been detected. © 2010 Elsevier B.V. All rights reserved.","author":[{"dropping-particle":"","family":"La Torre","given":"Olalla","non-dropping-particle":"De","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Renz","given":"Michael","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Corma","given":"Avelino","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Applied Catalysis A: General","id":"ITEM-2","issue":"1-2","issued":{"date-parts":[["2010"]]},"page":"165-171","publisher":"Elsevier B.V.","title":"Biomass to chemicals: Rearrangement of β-pinene epoxide into myrtanal with well-defined single-site substituted molecular sieves as reusable solid Lewis-acid catalysts","type":"article-journal","volume":"380"},"uris":["http://www.mendeley.com/documents/?uuid=6833c1a2-343c-41e8-886c-fde9fa26d01b"]}],"mendeley":{"formattedCitation":"[19,20]","plainTextFormattedCitation":"[19,20]","previouslyFormattedCitation":"[19,20]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[19,20]. Similarmente, el limoneno, que es un material renovable extraído de las cáscaras de naranjas, es epoxidado en óxido de limoneno, cuyo interés como material de partida en reacciones de isomerización ácida es bastante llamativa ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1016/j.mcat.2018.11.005","ISSN":"24688231","abstract":"Limonene oxidation over Cu-nanostructured mesoporous materials was studied. Three solids with different copper content were synthesized employing the template-ion exchange method, and physically-chemically analyzed by a multi-technical characterization. The performance of the molecular sieves as catalysts in the liquid phase oxyfunctionalization of limonene, employing hydrogen peroxide (H2O2) or t-butyl hydroperoxide (TBHP) as oxidants was evaluated. All synthesized Cu-MCM materials were active in the reaction. The obtained results showed that the used oxidant had an important influence on the products distribution under the employed conditions. With H2O2, compounds of high added value such as limonene oxide, carveol and carvone were mainly obtained. Meanwhile, with TBHP, limonene hydroperoxide turned out to be the major product. Finally, a reaction mechanism was proposed for each oxidant.","author":[{"dropping-particle":"","family":"Vaschetti","given":"Virginia M.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Cánepa","given":"Analía L.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Barrera","given":"Deicy","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Sapag","given":"Karim","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Eimer","given":"Griselda A.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Casuscelli","given":"Sandra G.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Molecular Catalysis","id":"ITEM-1","issue":"July","issued":{"date-parts":[["2018"]]},"page":"0-1","publisher":"Elsevier","title":"Limonene oxyfunctionalization over Cu-modified silicates employing hydrogen peroxide and t-Butyl hydroperoxide: Reaction pathway analysis","type":"article-journal"},"uris":["http://www.mendeley.com/documents/?uuid=d9583fdc-50a7-4082-9eb1-17cddb45c506"]},{"id":"ITEM-2","itemData":{"DOI":"10.1039/b418069k","ISBN":"1463-9262","ISSN":"1463-9262","PMID":"3210021","abstract":"The present review is emphasized on chemical aspects of epoxidation, environmental safety of promising methods for processing such a renewable raw material as terpenes. Various epoxidizing systems are considered, first of all those allowing one to perform catalytic epoxidation of terpenes, as well as their prospective value for commercial introduction. The review has included the materials published within the period from 1988 to 2008. For the convenience of comparing various epoxidizing systems and of choosing optimum conditions for the process carrying out, all the data are listed to form common tables. Key","author":[{"dropping-particle":"V","family":"Bakhvalov","given":"O","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"V","family":"Fomenko","given":"V","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Salakhutdinov","given":"N F","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Chemistry for Sustainable Development","id":"ITEM-2","issued":{"date-parts":[["2008"]]},"page":"633-691","title":"Modern Methods for the Epoxidation of α - and β -Pinenes , 3-Carene and Limonene","type":"article-journal","volume":"16"},"uris":["http://www.mendeley.com/documents/?uuid=5b50164a-f5eb-4625-b5dc-af4b9342efdf"]}],"mendeley":{"formattedCitation":"[21,22]","plainTextFormattedCitation":"[21,22]","previouslyFormattedCitation":"[21,22]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[21,22]. Un ejemplo es la producción de carvenona desde el epóxido de limoneno, el cual presenta numerosas aplicaciones en la industria de fragancias como perfume y también como saborizante ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.4236/ijoc.2013.33027","ISSN":"2161-4687","author":[{"dropping-particle":"","family":"Nguyen","given":"Thao-Tran Thi","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Chau","given":"Duy-Khiem Nguyen","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Duus","given":"Fritz","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Le","given":"Thach Ngoc","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"International Journal of Organic Chemistry","id":"ITEM-1","issue":"03","issued":{"date-parts":[["2013"]]},"page":"206-209","title":"Green Synthesis of Carvenone by Montmorillonite-Catalyzed Isomerization of 1,2-Limonene Oxide","type":"article-journal","volume":"03"},"uris":["http://www.mendeley.com/documents/?uuid=ac38d601-93f2-4afb-b69e-7d87da95ad9c"]}],"mendeley":{"formattedCitation":"[23]","plainTextFormattedCitation":"[23]","previouslyFormattedCitation":"[23]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[23]. Adicionalmente, el limoneno-1,2-diol que también se obtiene de la reacción de isomerización, es un bloque de construcción para la síntesis de diterpenos conocidos como Prevezol o también promisorios dado los centros estereogénicos presentes en su estructura ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1016/S0040-4039(01)01037-1","ISSN":"00404039","abstract":"When HgCl2 was added to a diastereomeric mixture of cis- and trans-(4S)-limonene 1,2-epoxide, the Hg(II) ions stereoselectively complexed to the cis epoxide, enabling ring opening by water. The resulting mercuric salt could be demetalated by treatment with NaBH4, giving a mixture of diastereomeric (1S,2S,4S)- and (1R,2R,4S)-diols. The remaining trans-(4S)-epoxide was obtained in >98% d.e. and 40% yield. For reactions on a larger scale, the most convenient reaction system was Hg(OAc)2 in 50% acetone/tris-HCl buffer pH 7.0. The reaction rate was affected by the pH, with pH 6-8 as optimum. © 2001 Elsevier Science Ltd. All rights reserved.","author":[{"dropping-particle":"","family":"Werf","given":"Mariët J.","non-dropping-particle":"Van der","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Jongejan","given":"Hugo","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Franssen","given":"Maurice C.R.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Tetrahedron Letters","id":"ITEM-1","issue":"32","issued":{"date-parts":[["2001"]]},"page":"5521-5524","title":"Resolution of limonene 1,2-epoxide diastereomers by mercury(II) ions","type":"article-journal","volume":"42"},"uris":["http://www.mendeley.com/documents/?uuid=e3d0de06-398f-4a2e-82bb-26e234b84399"]},{"id":"ITEM-2","itemData":{"DOI":"10.1080/00397919608004581","ISSN":"00397911","abstract":"In this paper we report a simple methodology for obtaining (+) trans - 1,2 - epoxylimonene (1b) in high purity (>99% HRGC) and reasonable quantity. The mixture of 1a and 1b in CH2Cl2 is stirred with 1M NaHSO3 in water. Under these conditions 1a is completely destroyed, while 1b is only partially destroyed .","author":[{"dropping-particle":"","family":"Santos","given":"Alexandre G.","non-dropping-particle":"Dos","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Lima Castro","given":"Fernando","non-dropping-particle":"De","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Jones","given":"Joel","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Synthetic Communications","id":"ITEM-2","issue":"14","issued":{"date-parts":[["1996"]]},"page":"2651-2656","title":"A simple method for producing pure (+) trans- 1,2-epoxylimonene","type":"article-journal","volume":"26"},"uris":["http://www.mendeley.com/documents/?uuid=d59faa0a-b134-40f5-a1b5-0d2eac2c85bd"]},{"id":"ITEM-3","itemData":{"DOI":"10.1021/ol400754e","ISSN":"15237060","abstract":"The first enantioselective synthesis of the proposed relative structures of Prevezol C is reported in 11 linear steps from readily available materials. The unusual syn bromohydrin was installed via a multistep sequence culminating in a diastereoselective geminal dibromide reduction. Discrepancies in the spectral data of the synthetic materials and the natural sample have led to the conclusion that the proposed structures are incorrect. © 2013 American Chemical Society.","author":[{"dropping-particle":"","family":"Leung","given":"Anna E.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Blair","given":"Michael","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Forsyth","given":"Craig M.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Tuck","given":"Kellie L.","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Organic Letters","id":"ITEM-3","issue":"9","issued":{"date-parts":[["2013"]]},"page":"2198-2201","title":"Synthesis of the proposed structures of Prevezol C","type":"article-journal","volume":"15"},"uris":["http://www.mendeley.com/documents/?uuid=6852379d-e632-427a-97e3-25cb21864359"]}],"mendeley":{"formattedCitation":"[24–26]","plainTextFormattedCitation":"[24–26]","previouslyFormattedCitation":"[24–26]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[24–26]. De hecho, la oxofuncionalización de tales monoterpenos produce compuestos con aplicabilidad en el sector de fragancias, sabores y sustancias activas terapéuticamente ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1021/acs.iecr.7b00789","ISSN":"15205045","abstract":"29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 2 ABSTRACT In this work, we investigate the influence of the Sn-loading and the pore size of MCM-41 materials on the catalytic nopol production. Sn(IV) was anchored onto MCM-41 by incipient wetness impregnation with metal coverages within 0.01 and 0.5 Sn nm -2 (i.e., below the monolayer content). We provide evidence that at coverages below 0.06 Sn nm -2 , Sn(IV) is predominantly present as isolated centers, whereas at higher coverages octahedral and/or oligomeric species are formed which exhibit lower catalytic activity. The rate of nopol production was ten times higher over Sn/MCM-41 than that of analogous Sn silica gel materials. The Turnover Frequency (TOF) features a maximum as a function of Sn coverage between 0.03 and 0.05 Sn nm -2 for Sn/MCM-41 catalysts and 0.15 Sn nm -2 for Sn silica gel materials. These results show that both the metal content and pore size can be tuned to enhance catalytic performance of Sn/MCM-41 materials.","author":[{"dropping-particle":"","family":"Casas-Orozco","given":"Daniel","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Alarcón","given":"Edwin","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Carrero","given":"Carlos A.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Venegas","given":"Juan M.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"McDermott","given":"William","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Klosterman","given":"Ellen","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Hermans","given":"Ive","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Villa","given":"Aída Luz","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Industrial and Engineering Chemistry Research","id":"ITEM-1","issue":"23","issued":{"date-parts":[["2017"]]},"page":"6590-6598","title":"Influence of Tin Loading and Pore Size of Sn/MCM-41 Catalysts on the Synthesis of Nopol","type":"article-journal","volume":"56"},"uris":["http://www.mendeley.com/documents/?uuid=d928d562-2279-4669-9e46-20ca89660420"]}],"mendeley":{"formattedCitation":"[27]","plainTextFormattedCitation":"[27]","previouslyFormattedCitation":"[27]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[27]. Es por esto que, el acoplamiento de reacciones secuenciales que involucren la epoxidación e isomerización mediante estrategias one-pot a partir de compuestos derivados de la biomasa, como el β-pineno y limoneno, puede potenciar el uso de procedimientos ambientalmente sostenibles. Para ello la catálisis heterogénea juega un rol importante, porque con el uso de materiales multifuncionales que incluyen un soporte y varios sitios activos, se pueden promover múltiples reacciones en un mismo reactor ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.3390/catal10030309","ISSN":"20734344","abstract":"A family of heterometallic metal-organic frameworks (MOFs) (CPM200s) harmoniously coexisting as Lewis acids and base (azo) sites were prepared. Seven CPM200s were employed as multifunctional heterogeneous cascade catalysts for the one-pot deacetalization-Knoevenagel reaction in a solvent-free system. Benefiting from the cooperation between Lewis acids from the open metal sites and base sites from the ligands, the CPM200s showed high activity and selectivity for the tandem reaction. The heterometallic 3D porous framework reported here not only offers a combination of two opposite active sites in the same framework of materials but also increases mass transfer of the substrate, thus maximizing the efficiency and substrate selectivity of the bifunctional catalysts. The CPM200s showed the highest turnover frequency (TOF), outperforming that of the reported MOFs in tandem with the deacetalization-Knoevenagel reaction. A strong correlation between the TOF and charge-to-radius ratio (z/r) of metal ions in the CPM200s was observed for the first time. The bifunctional CPM200s catalysts can be reused five times without significant loss of activity.","author":[{"dropping-particle":"","family":"Zheng","given":"Mingming","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Wang","given":"Yanxiang","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Feng","given":"Pingyun","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Catalysts","id":"ITEM-1","issue":"3","issued":{"date-parts":[["2020"]]},"title":"Bifunctional heterometallic metal-organic frameworks for solvent-free heterogeneous cascade catalysis","type":"article-journal","volume":"10"},"uris":["http://www.mendeley.com/documents/?uuid=95673c0e-0f0f-466e-a3df-bcec74584a94"]}],"mendeley":{"formattedCitation":"[28]","plainTextFormattedCitation":"[28]","previouslyFormattedCitation":"[28]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[28]. Adicionalmente, tales materiales pueden ser usados a gran escala varias veces, lo que es atractivo desde el punto de vista de la ingeniería, la química verde y sostenible y, además, permiten la disminución de costos de producción y generan rentabilidad económica, lo cual resulta una gran ventaja con respecto a catalizadores que son desarrollados para solo una etapa de reacción ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1002/9783527610044","ISSN":"10855629","author":[{"dropping-particle":"","family":"Boudart","given":"James A. Dumesic George W. Huber Michel","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Handbook of Heterogeneous Catalysis: Online","id":"ITEM-1","issue":"1","issued":{"date-parts":[["2008"]]},"page":"1-2","title":"Principles of heterogeneous catalysis","type":"article-journal","volume":"30"},"uris":["http://www.mendeley.com/documents/?uuid=398b9549-6f99-4c68-98e7-e80a626cf370"]}],"mendeley":{"formattedCitation":"[29]","plainTextFormattedCitation":"[29]","previouslyFormattedCitation":"[29]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[29]. Por ejemplo, 80-90% de la fabricación de sustancias químicas, son procesos basados en el uso de catalizadores los cuales generan ganancias de aproximadamente 1.5 billones de dólares alrededor del mundo ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1039/c9sc05947d","ISSN":"20416539","abstract":"Despite the indisputable success of conventional approaches to manipulate the performance of heterogeneous catalysts by tuning the composition and structure of active sites, future research on catalysis engineering will likely go beyond the catalyst itself. Recently, several auxiliary promotion methods, either promoting the activity of reagents or enabling optimized adsorbate-catalyst interactions, have been proven as viable strategies to enhance catalytic reactions. Those auxiliary promotion methods range from electric/magnetic fields and electric potentials to mechanic stress, significantly altering the properties of reagent molecules and/or the surface characteristics of nanostructured catalysts. Apart from static enhancement effects, they in principle also allow for spatially and temporally variable modifications of catalyst surfaces. While some of those methods have been demonstrated, some are only theoretically predicted, opening exciting avenues for future experimental advances. Besides fundamental descriptions and comparisons of each activation method, in this perspective we plan to provide examples for the applications of those techniques for a variety of catalytic reactions as diverse as N2 and CO2 hydrogenation as well as electrochemical water splitting. Finally, we provide a unifying view and guidelines for future research into the use of promotion methods, generating deeper understanding of the complex dynamics on the nanoparticle surface under auxiliary promotion and the expansion of auxiliary techniques to different sustainability-related reactions.","author":[{"dropping-particle":"","family":"Hülsey","given":"Max J.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Lim","given":"Chia Wei","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Yan","given":"Ning","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Chemical Science","id":"ITEM-1","issue":"6","issued":{"date-parts":[["2020"]]},"page":"1456-1468","title":"Promoting heterogeneous catalysis beyond catalyst design","type":"article-journal","volume":"11"},"uris":["http://www.mendeley.com/documents/?uuid=0010f17f-8987-4070-b10c-95f114527a2f"]}],"mendeley":{"formattedCitation":"[30]","plainTextFormattedCitation":"[30]","previouslyFormattedCitation":"[30]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[30]. Considerando lo anterior, diferentes estrategias para el uso de catalizadores heterogéneos han sido desarrolladas; sin embargo, su aplicabilidad en reacciones one-pot usando los monoterpenos β-pineno y limoneno son escasas y limitadas. Por otro lado, muchas de estos procedimientos carecen de acoplamientos con la búsqueda de los factores químicos que las afectan, así como detalles computacionales que permitan elucidar los mecanismos de reacción. Es de este modo que los grupos de Investigación Catálisis Ambiental de la Universidad de Antioquia (GCA) y el Grupo de Investigación Fitoquímica Universidad Javeriana (GIFUJ), se encuentran desarrollando propuestas de mecanismo de reacción en química orgánica. Recientemente, se desarrolló en conjunto una investigación para la determinación del mecanismo de reacción de la isomerización de los epóxidos de α- y β-pineno usando Fe3+ como sitio activo catalítico ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1021/acs.jpca.9b09622","ISSN":"1089-5639","author":[{"dropping-particle":"","family":"Sánchez-Velandia","given":"Julián Eduardo","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Mejía Chica","given":"Sol M.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Villa Holguín","given":"Aída Luz","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"The Journal of Physical Chemistry A","id":"ITEM-1","issued":{"date-parts":[["2020"]]},"title":" Reaction Mechanism of the Isomerization of Monoterpenes Epoxides with Fe 3+ as Active Catalytic Specie. A Computational Approach ","type":"article-journal"},"uris":["http://www.mendeley.com/documents/?uuid=fa9026d6-2117-46f0-b1bc-085c987c701a"]}],"mendeley":{"formattedCitation":"[31]","plainTextFormattedCitation":"[31]","previouslyFormattedCitation":"[31]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[31]. Adicionalmente, se encuentran en desarrollo otras dos propuestas mecanísticas, acoplando en conjunto a los datos experimentales, cálculos del tipo DFT (Density Functional Theory) en la isomerización del epóxido de limoneno y condensaciones de monoterpenos con aldehídos. En este sentido, el grupo de Investigación Catálisis Ambiental, adelanta investigaciones relacionados con el desarrollo de catalizadores quimioselectivos multifuncionales y su aplicación en reacciones one-pot en la transformación de monoterpenos, además, que cuenta con amplia experiencia en reacciones de condensación tipo Prins entre β-pineno y paraformaldehído ADDIN CSL_CITATION {"citationItems":[{"id":"ITEM-1","itemData":{"DOI":"10.1021/acs.iecr.7b00789","ISSN":"15205045","abstract":"29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 2 ABSTRACT In this work, we investigate the influence of the Sn-loading and the pore size of MCM-41 materials on the catalytic nopol production. Sn(IV) was anchored onto MCM-41 by incipient wetness impregnation with metal coverages within 0.01 and 0.5 Sn nm -2 (i.e., below the monolayer content). We provide evidence that at coverages below 0.06 Sn nm -2 , Sn(IV) is predominantly present as isolated centers, whereas at higher coverages octahedral and/or oligomeric species are formed which exhibit lower catalytic activity. The rate of nopol production was ten times higher over Sn/MCM-41 than that of analogous Sn silica gel materials. The Turnover Frequency (TOF) features a maximum as a function of Sn coverage between 0.03 and 0.05 Sn nm -2 for Sn/MCM-41 catalysts and 0.15 Sn nm -2 for Sn silica gel materials. These results show that both the metal content and pore size can be tuned to enhance catalytic performance of Sn/MCM-41 materials.","author":[{"dropping-particle":"","family":"Casas-Orozco","given":"Daniel","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Alarcón","given":"Edwin","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Carrero","given":"Carlos A.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Venegas","given":"Juan M.","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"McDermott","given":"William","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Klosterman","given":"Ellen","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Hermans","given":"Ive","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Villa","given":"Aída Luz","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Industrial and Engineering Chemistry Research","id":"ITEM-1","issue":"23","issued":{"date-parts":[["2017"]]},"page":"6590-6598","title":"Influence of Tin Loading and Pore Size of Sn/MCM-41 Catalysts on the Synthesis of Nopol","type":"article-journal","volume":"56"},"uris":["http://www.mendeley.com/documents/?uuid=d928d562-2279-4669-9e46-20ca89660420"]},{"id":"ITEM-2","itemData":{"DOI":"10.1016/j.fuel.2014.08.067","ISBN":"0016-2361","ISSN":"00162361","abstract":"The kinetics of the catalytic synthesis of nopol from β-pinene and paraformaldehyde over Sn-MCM-41 catalyst and using ethyl acetate as solvent is presented and compared with previous studies in toluene. Reaction rate data were fitted to a kinetic expression based on the Langmuir-Hinshelwood formalism, using the initial rates method. Reaction rate constant and adsorption constants were determined by regression of experimental data. The highest adsorption constant for nopol respect to reactants (KC = 14.948 M-1) allows to explain the strong inhibition effect of this compound that is experimentally observed. Solvent effects were discussed in terms of formaldehyde solubility, solvation of activated complex and reactants, and competitive adsorption on active sites. Higher solubility of formaldehyde in ethyl acetate respect to toluene, determined with Henry's law, along with the competitive adsorption of solvent and a more probable solvation of β-pinene and nopol may explain the better selectivity in ethyl acetate. Dependency of reaction constant on temperature was evaluated between 75 °C and 90 °C, resulting in an apparent activation energy of 98 kJ mol-1, which is higher than in toluene, suggesting stabilization of carbocation intermediates by solvation in the polar ethyl acetate solvent.","author":[{"dropping-particle":"","family":"Casas-Orozco","given":"Daniel","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Alarcón","given":"Edwin","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Villa","given":"Aída Luz","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Fuel","id":"ITEM-2","issued":{"date-parts":[["2015"]]},"page":"130-137","title":"Kinetic study of the nopol synthesis by the Prins reaction over tin impregnated MCM-41 catalyst with ethyl acetate as solvent","type":"article-journal","volume":"149"},"uris":["http://www.mendeley.com/documents/?uuid=3fd61eb9-3b90-49fe-99d4-66f6f2506d0f"]},{"id":"ITEM-3","itemData":{"DOI":"10.1021/acs.iecr.7b00789","ISSN":"0888-5885","abstract":"29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 2 ABSTRACT In this work, we investigate the influence of the Sn-loading and the pore size of MCM-41 materials on the catalytic nopol production. Sn(IV) was anchored onto MCM-41 by incipient wetness impregnation with metal coverages within 0.01 and 0.5 Sn nm -2 (i.e., below the monolayer content). We provide evidence that at coverages below 0.06 Sn nm -2 , Sn(IV) is predominantly present as isolated centers, whereas at higher coverages octahedral and/or oligomeric species are formed which exhibit lower catalytic activity. The rate of nopol production was ten times higher over Sn/MCM-41 than that of analogous Sn silica gel materials. The Turnover Frequency (TOF) features a maximum as a function of Sn coverage between 0.03 and 0.05 Sn nm -2 for Sn/MCM-41 catalysts and 0.15 Sn nm -2 for Sn silica gel materials. These results show that both the metal content and pore size can be tuned to enhance catalytic performance of Sn/MCM-41 materials.","author":[{"dropping-particle":"","family":"Casas-Orozco","given":"Daniel","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Alarcón","given":"Edwin","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Carrero","given":"Carlos A","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Venegas","given":"Juan M","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Mcdermott","given":"William P","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Klosterman","given":"Ellen","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Hermans","given":"Ive","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Villa","given":"Aída-Luz","non-dropping-particle":"","parse-names":false,"suffix":""},{"dropping-particle":"","family":"Mcdermott","given":"William","non-dropping-particle":"","parse-names":false,"suffix":""}],"container-title":"Ind. Eng. Chem. Res","id":"ITEM-3","issued":{"date-parts":[["2017"]]},"title":"The Influence of Tin Loading and Pore Size of Sn/ MCM-41 Catalysts on the Synthesis of Nopol The Influence of Tin Loading and Pore Size of Sn/MCM-41 Catalysts on the Synthesis of Nopol","type":"article-journal"},"uris":["http://www.mendeley.com/documents/?uuid=e90145fc-6e1f-4bd4-a4fb-8a543e080ad3"]}],"mendeley":{"formattedCitation":"[27,32,33]","plainTextFormattedCitation":"[27,32,33]","previouslyFormattedCitation":"[27,32,33]"},"properties":{"noteIndex":0},"schema":"https://github.com/citation-style-language/schema/raw/master/csl-citation.json"}[27,32,33]. Por otro lado, la colaboración por parte de la Universidad Andrés Bello (Chile), fortalecería el uso de herramientas computacionales con el objetivo de obtener información de funciones de reactividad y su evolución a medida que se dan los mecanismos de reacción, así como el modelar sistemas catalíticos más complejos (en forma de clúster), que, a su vez, reflejan en gran medida los catalizadores que se seleccionarían para el desarrollo de las rutas mecanísticas de las reacciones one-pot. Con base en lo anterior, en la presente propuesta de investigación posdoctoral, se pretende responder a la pregunta: ¿Cuáles son las condiciones de reacción y mecanismo de reacción que permitan obtener selectivamente compuestos de alto valor agregado a partir de reacciones one-pot (oxidación/epoxidación junto con la isomerización) con monoterpenos (β-pineno, y limoneno) usando catalizadores multifuncionales? Por otro lado, el presente estudio permitirá proponer sistemas heterogéneos selectivos y, además, con condiciones de reacción acorde con los principios de la química verde y sostenible, con potencial aplicación en química fina. Adicionalmente, la formación del investigador posdoctoral, permitirá el fortalecimiento de los vínculos científicos y colaboración académica entre la Pontificia Universidad Javeriana (Bogotá-Colombia), Universidad de Antioquia (Medellín-Colombia) y Universidad Andrés Bello (Chile). Esta integración, permitirá garantizar un excelente equipo de trabajo para la investigación del postdoctor, así como el desarrollo exitoso de la propuesta dada la experiencia previa en el campo de la química computacional y la catálisis heterogénea de dicho postdoctor.