Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)aniline
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Otros documentos de la autoría: Maciá Delgado, María; Porcar Garcia, Raul; Martí-Centelles, Vicente; Garcia-Verdugo, Eduardo; Burguete, M. Isabel; Luis, Santiago V.
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Título
Rational Design of Simple Organocatalysts for the HSiCl3 Enantioselective Reduction of (E)-N-(1-Phenylethylidene)anilineAutoría
Fecha de publicación
2021-11-18Editor
MDPIISSN
1420-3049Cita bibliográfica
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/molecules26226963Tipo de documento
info:eu-repo/semantics/articleVersión
info:eu-repo/semantics/publishedVersionPalabras clave / Materias
Resumen
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 ... [+]
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. [-]
Publicado en
Molecules, Vol. 26, Iss. 22 (November-2 2021)Entidad financiadora
Generalitat Valenciana | Universitat Jaume I | Ministerio de Ciencia, Innovación y Universidades
Código del proyecto o subvención
PROMETEO/2016/071 | AICO/2021/139 | UJI-B2019-40 | RTI2018- 098233-B-C22 | CIDEGENT/2020/031
Título del proyecto o subvención
Una aproximación a la sostenibilidad basada en sistemas multi-catalíticos inspirados en el modelo celular-syncell | Líquidos iónicos y materiales relacionados para aplicaciones farmacológicas | Pla de Promoció de la Investigació de la Universitat Jaume I | CO2 activation by enzymatic mimics based on pseudopeptidic macrocycles | Nuevos procesos multi-catalíticos verdes basados en la tecnología de los líquidos iónicos: desde las materias primas sencillas hasta los químicos con valor añadido (greencatils)
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