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Scientific article
Letter
English

Asymmetric Michael addition of α-hydroxy aldehydes to nitroolefins catalyzed by chiral diamine

Published inOrganic letters, vol. 5, no. 14, p. 2559-2561
Publication date2003
Abstract

The regio-, stereo-, and enantioselective direct Michael addition of alpha-hydroxyketones to beta-arylnitroolefins catalyzed by N-iPr-2,2'-bipyrrolidine is described. The formation of an internal hydrogen bond between the OH group of alpha-hydoxyacetone and the tertiary nitrogen of the catalyst leads to the formation of a rigid cis enamine intermediate that explains the inversion of the expected diastereoselectivity and the very high ee's.

Citation (ISO format)
ANDREY, Olivier, ALEXAKIS, Alexandre, BERNARDINELLI, Gérald Hugues. Asymmetric Michael addition of α-hydroxy aldehydes to nitroolefins catalyzed by chiral diamine. In: Organic letters, 2003, vol. 5, n° 14, p. 2559–2561. doi: 10.1021/ol0348755
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ISSN of the journal1523-7052
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