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Asymmetric Conjugate Addition to α-Substituted Enones/Enolate Trapping

Abstract : 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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Submitted on : Thursday, March 5, 2015 - 11:48:46 AM
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Nicolas Germain, Laure Guénée, Marc Mauduit, Alexandre Alexakis. Asymmetric Conjugate Addition to α-Substituted Enones/Enolate Trapping. Letters in Organic Chemistry, Bentham Science Publishers, 2014, 16 (1), pp.118-121. ⟨10.1021/ol403104s⟩. ⟨hal-01123659⟩



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