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. 2007 Sep 13;9(19):3749-52.
doi: 10.1021/ol7015498. Epub 2007 Aug 23.

First enantioselective organocatalytic conjugate addition of aldehydes to vinyl phosphonates

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First enantioselective organocatalytic conjugate addition of aldehydes to vinyl phosphonates

Sarah Sulzer-Mossé et al. Org Lett. .

Abstract

Chiral amines catalyze the enantioselective conjugate addition of aldehydes to vinyl phosphonates in high yields and with enantioselectivities up to 97% ee. This novel process provides synthetically useful chiral gamma-geminal phosphonate aldehydes which can be easily converted in a few steps into chiral beta-substituted vinyl phosphonates with conservation of the optical purity.

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