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

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Published in Organic Letters. 2003, vol. 5, no. 14, p. 2559-2561
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.
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PMID: 12841780
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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. https://archive-ouverte.unige.ch/unige:8039

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Deposited on : 2010-06-21

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