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Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline

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Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline

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dc.contributor.author Maciá, María es_ES
dc.contributor.author Porcar, Raúl es_ES
dc.contributor.author Martí-Centelles, Vicente es_ES
dc.contributor.author García-Verdugo, Eduardo es_ES
dc.contributor.author Burguete, Maria Isabel es_ES
dc.contributor.author Luis, Santiago V. es_ES
dc.date.accessioned 2023-04-06T18:00:59Z
dc.date.available 2023-04-06T18:00:59Z
dc.date.issued 2021-11 es_ES
dc.identifier.uri http://hdl.handle.net/10251/192745
dc.description.abstract [EN] Prolinamides are well-known organocatalysts for the HSiCl3 reduction of imines; however, custom design of catalysts is based on trial-and-error experiments. In this work, we have used a combination of computational calculations and experimental work, including kinetic analyses, to properly understand this process and to design optimized catalysts for the benchmark (E)-N-(1-phenylethylidene)aniline. The best results have been obtained with the amide derived from 4-methoxyaniline and the N-pivaloyl protected proline, for which the catalyzed process is almost 600 times faster than the uncatalyzed one. Mechanistic studies reveal that the formation of the component supramolecular complex catalyst-HSiCl3-substrate, involving hydrogen bonding breaking and costly conformational changes in the prolinamide, is an important step in the overall process. es_ES
dc.description.sponsorship This research was funded by Generalitat Valenciana, grant number PROMETEO/2016/071 and AICO/2021/139, Pla de Promocio de la Investigacio de la Universitat Jaume I, grant number UJI-B2019-40 and Ministerio de Ciencia, Innovacion y Universidades, grant number RTI2018098233-B-C22. V.M.-C. acknowledges the financial support from Generalitat Valenciana (CIDEGENT/2020/031). es_ES
dc.language Inglés es_ES
dc.publisher MDPI AG es_ES
dc.relation.ispartof Molecules es_ES
dc.rights Reconocimiento (by) es_ES
dc.subject Organocatalysis es_ES
dc.subject Asymmetric catalysis es_ES
dc.subject Trichlorosilane es_ES
dc.subject Imine reduction es_ES
dc.subject Mechanistic studies es_ES
dc.title Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.3390/molecules26226963 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GV INNOV.UNI.CIENCIA//CIDEGENT%2F2020%2F031//CAJAS ORGANICAS COMO CONTENEDORES PARA LIBERACION DIRIGIDA DE FARMACOS EN TERAPIA CONTRA EL CANCER/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-098233-B-C22/ES/NUEVOS PROCESOS MULTI-CATALITICOS VERDES BASADOS EN LA TECNOLOGIA DE LOS LIQUIDOS IONICOS: DESDE LAS MATERIAS PRIMAS SENCILLAS HASTA LOS QUIMICOS CON VALOR AÑADIDO/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//AICO%2F2021%2F139/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//PROMETEO%2F2016%2F071//Una aproximación a la sostenibilidad basa en sistemes mult-catalíticos inspirados en el modelo celuar-syncell/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/UJI//UJI-B2019-40/ es_ES
dc.rights.accessRights Abierto es_ES
dc.description.bibliographicCitation Maciá, M.; Porcar, R.; Martí-Centelles, V.; García-Verdugo, E.; Burguete, MI.; Luis, SV. (2021). Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline. Molecules. 26(22):1-19. https://doi.org/10.3390/molecules26226963 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.3390/molecules26226963 es_ES
dc.description.upvformatpinicio 1 es_ES
dc.description.upvformatpfin 19 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 26 es_ES
dc.description.issue 22 es_ES
dc.identifier.eissn 1420-3049 es_ES
dc.identifier.pmid 34834055 es_ES
dc.identifier.pmcid PMC8625272 es_ES
dc.relation.pasarela S\450936 es_ES
dc.contributor.funder Universitat Jaume I es_ES
dc.contributor.funder GENERALITAT VALENCIANA es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES


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