Enantioselective catalytic reduction of ketoimines with trichlorosilane promoted by readily available chiral Lewis bases.

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.

journal_name

Chirality

journal_title

Chirality

authors

Guizzetti S,Benaglia M,Cozzi F,Rossi S,Celentano G

doi

10.1002/chir.20615

subject

Has Abstract

pub_date

2009-01-01 00:00:00

pages

233-8

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

21

pub_type

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