☆ 4.7 Article

Stereoselective Lewis Base-Catalyzed Asymmetric Hydrosilylation of α-Acetamido-β-enamino Esters: Straightforward Approach for the Construction of α,β-Diamino Acid Derivatives

ADVANCED SYNTHESIS & CATALYSIS (2013)

Journal

ADVANCED SYNTHESIS & CATALYSIS

Volume 355, Issue 10, Pages 1931-1936

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/adsc.201300184

Keywords

amino acids; asymmetric catalysis; hydrosilylation; Lewis bases

Categories

Chemistry, Applied Chemistry, Organic

Funding

National Sciences Foundation of China [20972155, 21172217]
National Basic Research Program of China (973 Program) [2010CB833300]

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Abstract

The Lewis base-organocatalyzed asymmetric hydrosilylation of alpha-acetamido-beta-enamino esters was investigated. Among various chiral Lewis base catalysts, a novel catalyst derived from L-serine was found to be the most efficient one which can promote the reaction to afford a series of alpha,beta-diamino acid derivatives with high yields (up to 99%), excellent enantioselectivities (up to 98% ee) and moderate diastereoselectivities (up to 80: 20 dr). The absolute configuration of one of the products was determined by the X-ray crystallographic analysis. In addition, the mechanism and the transition state of the reaction were proposed.

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