The straightforward synthesis of a series of enantiomerically pure Lewis basic amides by simple condensation of commercially available enantiopure diamines with picolinic acid is reported. These compounds were shown to promote the enantioselective reduction of ketoimines with trichlorosilane. Working with the model substrate N-phenyl benzophenone imine, the new organocatalysts led to the formation of the corresponding amine, with excellent chemical efficiency (up to 99% chemical yield) and good stereoselectivity (up to 73% ee). Up to 83% of enantioselectivity was reached in the reduction of differently substituted imines.

Enantioselective Catalytic Reduction of Ketoimines with Trichlorosilane Promoted by Readily Available Chiral Lewis Bases / S. Guizzetti, M. Benaglia, F. Cozzi, S. Rossi, G. Celentano. - In: CHIRALITY. - ISSN 1520-636X. - 21:1 Special Issue(2009 Jan), pp. 233-238. [10.1002/chir.20615]

Enantioselective Catalytic Reduction of Ketoimines with Trichlorosilane Promoted by Readily Available Chiral Lewis Bases

S. Guizzetti
Primo
;
M. Benaglia
Secondo
;
F. Cozzi;S. Rossi
Penultimo
;
G. Celentano
Ultimo
2009

Abstract

The straightforward synthesis of a series of enantiomerically pure Lewis basic amides by simple condensation of commercially available enantiopure diamines with picolinic acid is reported. These compounds were shown to promote the enantioselective reduction of ketoimines with trichlorosilane. Working with the model substrate N-phenyl benzophenone imine, the new organocatalysts led to the formation of the corresponding amine, with excellent chemical efficiency (up to 99% chemical yield) and good stereoselectivity (up to 73% ee). Up to 83% of enantioselectivity was reached in the reduction of differently substituted imines.
organic catalysis; Lewis bases; trichlorosilane; enantioselectivity; chiral amines; Catalysis; Imines; Molecular Conformation; Oxidation-Reduction; Silanes; Stereoisomerism; Substrate Specificity;
Settore CHIM/06 - Chimica Organica
11-set-2008
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/946310
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