Chemical Communications 2008-09-28

Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane.

Masaharu Sugiura, Norimasa Sato, Shunsuke Kotani, Makoto Nakajima

Index: Chem. Commun. (Camb.) (36) , 4309-11, (2008)

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Abstract

Lewis bases such as Ph3P=O and HMPA catalyze the 1,4-reduction of alpha,beta-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.