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Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline
dc.contributor.author | Maciá Delgado, María | |
dc.contributor.author | Porcar Garcia, Raul | |
dc.contributor.author | Martí-Centelles, Vicente | |
dc.contributor.author | Garcia-Verdugo, Eduardo | |
dc.contributor.author | Burguete, M. Isabel | |
dc.contributor.author | Luis, Santiago V. | |
dc.date.accessioned | 2022-07-08T13:22:06Z | |
dc.date.available | 2022-07-08T13:22:06Z | |
dc.date.issued | 2021-11-18 | |
dc.identifier.citation | Maciá, M.; Porcar, R.; Martí-Centelles, V.; García-Verdugo, E.; Burguete, M.I.; Luis, S.V. Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1- Phenylethylidene)aniline. Molecules 2021, 26, 6963. https://doi.org/ 10.3390/molecules26226963 | ca_CA |
dc.identifier.issn | 1420-3049 | |
dc.identifier.uri | http://hdl.handle.net/10234/198244 | |
dc.description.abstract | 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. | ca_CA |
dc.format.extent | 19 p. | ca_CA |
dc.format.mimetype | application/pdf | ca_CA |
dc.language.iso | eng | ca_CA |
dc.publisher | MDPI | ca_CA |
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dc.relation | Pla de Promoció de la Investigació de la Universitat Jaume I | ca_CA |
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dc.relation.isPartOf | Molecules, Vol. 26, Iss. 22 (November-2 2021) | ca_CA |
dc.rights | Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/4.0/). | ca_CA |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | ca_CA |
dc.subject | organocatalysis | ca_CA |
dc.subject | asymmetric catalysis | ca_CA |
dc.subject | trichlorosilane | ca_CA |
dc.subject | imine reduction | ca_CA |
dc.subject | mechanistic studies | ca_CA |
dc.title | Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline | ca_CA |
dc.type | info:eu-repo/semantics/article | ca_CA |
dc.identifier.doi | https://doi.org/ 10.3390/molecules26226963 | |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | ca_CA |
dc.type.version | info:eu-repo/semantics/publishedVersion | ca_CA |
project.funder.name | Generalitat Valenciana | ca_CA |
project.funder.name | Universitat Jaume I | ca_CA |
project.funder.name | Ministerio de Ciencia, Innovación y Universidades | ca_CA |
oaire.awardNumber | PROMETEO/2016/071 | ca_CA |
oaire.awardNumber | AICO/2021/139 | ca_CA |
oaire.awardNumber | UJI-B2019-40 | ca_CA |
oaire.awardNumber | RTI2018- 098233-B-C22 | ca_CA |
oaire.awardNumber | CIDEGENT/2020/031 | ca_CA |
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