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Asymmetric Conjugate Addition to α-Substituted Enones/Enolate Trapping

By Nicolas Germain, Laure Guénée, Marc Mauduit and Alexandre Alexakis

Abstract

International audienceAn NHC–Cu complex catalyzed the asymmetric conjugate addition (ACA) of various Grignard reagents to nonactivated α-substituted cyclic enones to give 2,3-dialkylated cyclopentanones and cyclohexanones. The Michael addition features the formation of a magnesium enolate intermediate. One-pot diastereoselective trapping of this enolate by alkyl, propargyl, allyl, and benzyl halides led to ketones with contiguous α-quaternary and β-tertiary centers

Topics: [ CHIM.CATA ] Chemical Sciences/Catalysis
Publisher: Bentham Science Publishers
Year: 2014
DOI identifier: 10.1021/ol403104s
OAI identifier: oai:HAL:hal-01123659v1
Provided by: Hal-Diderot
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