Issue 36, 2008

Lewis base-catalyzed conjugate reduction and reductive aldol reaction of α,β-unsaturated ketones using trichlorosilane

Abstract

Lewis bases such as Ph3P[double bond, length as m-dash]O and HMPA catalyze the 1,4-reduction of α,β-unsaturated ketones with trichlorosilane, and because the 1,2-reduction of aldehydes scarcely proceeded under the conditions, one-pot reductive aldol reactions with aldehydes were successfully achieved; preliminary studies using a chiral Lewis base revealed a high potential for enantioselective catalysis.

Graphical abstract: Lewis base-catalyzed conjugate reduction and reductive aldol reaction of α,β-unsaturated ketones using trichlorosilane

Supplementary files

Article information

Article type
Communication
Submitted
02 May 2008
Accepted
03 Jun 2008
First published
17 Jul 2008

Chem. Commun., 2008, 4309-4311

Lewis base-catalyzed conjugate reduction and reductive aldol reaction of α,β-unsaturated ketones using trichlorosilane

M. Sugiura, N. Sato, S. Kotani and M. Nakajima, Chem. Commun., 2008, 4309 DOI: 10.1039/B807529H

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