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Asymmetric conjugate addition to α-substituted enones/enolate trapping. 2014

Nicolas Germain, and Laure Guénée, and Marc Mauduit, and Alexandre Alexakis
Department of Organic Chemistry, University of Geneva , Quai Ernest Ansermet, 30, 1211 Geneva 4, Switzerland.

An 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.

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