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Synfacts 2006(9): 0913-0913  
DOI: 10.1055/s-2006-949261
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Conjugate Addition of Organozinc Reagents to Enones

Contributor(s): Mark Lautens, Andrew Martins
K-S. Lee, M. K. Brown, A. W. Hird, A. H. Hoveyda*
Boston College, Chestnut Hill, USA
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Using a chiral, N-heterocyclic carbene (NHC)-Cu(I) catalyst formed in situ, cyclic β-substituted enones can be enantioselectively alkylated at the β-position with organozinc reagents to generate chiral all-carbon quaternary centers. Both alkyl- and arylzinc species worked well, affording products in good to excellent yields and enantioselectivities. Interestingly, alkylzinc and arylzinc reagents react with an opposite sense of chirality.