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Enantioselective catalytic reduction of ketoimines with trichlorosilane promoted by readily available chiral Lewis bases
Author(s) -
Guizzetti Stefania,
Benaglia Maurizio,
Cozzi Franco,
Rossi Sergio,
Celentano Giuseppe
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20615
Subject(s) - trichlorosilane , chemistry , enantioselective synthesis , enantiopure drug , lewis acids and bases , imine , stereoselectivity , organic chemistry , chiral lewis acid , chirality (physics) , catalysis , pinacol , combinatorial chemistry , chiral symmetry breaking , physics , quantum mechanics , quark , silicon , nambu–jona lasinio model
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. Chirality, 2009. © 2008 Wiley‐Liss, Inc.