Rational Design of Simple Organocatalysts for the HSiCl 3 Enantioselective Reduction of (E)- N -(1-Phenylethylidene)aniline.

Autor:	Maciá, María, Porcar, Raúl, Martí-Centelles, Vicente, García-Verdugo, Eduardo, Burguete, Maria Isabel, Luis, Santiago V.
Předmět:	ANILINE CUSTOM design HYDROGEN bonding IMINES CATALYSTS
Zdroj:	Molecules; Nov2021, Vol. 26 Issue 22, p6963-6963, 1p
Abstrakt:	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. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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