Lewis base organocatalyzed enantioselective hydrosilylation of α-keto ketimines

Abstract

A chiral Lewis base organocatalyzed enantioselective hydrosilylation of α-keto ketimines was investigated. The reactions afforded various enantioenriched α-amino ketones with good yields(up to 95%) in moderate to good enantioselectivities(up to 98% e.e.). Furthermore, one of the products was reduced to a chiral 1,2-amino alcohol. Following cyclization of it with triphosgene generated a cannabinoid receptor 1(CB1) inhibitor with good diastereoselectivity.

Keywords

Amino alcohol / Asymmetric catalysis / Hydrosilylation

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