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Updated: Sep 23, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Asymmetric Michael addition of alpha-hydroxyketones to nitroolefins catalyzed by chiral diamine
Olivier Andrey1, Alexandre Alexakis, Gérald Bernardinelli
1Chimie Organique, Sciences II, University of Geneva, Quai Ernest Ansermet, CH-1211, Geneva, Switzerland.
Abstract:
[reaction: see text] 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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