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Synfacts 2007(5): 0516-0516
DOI: 10.1055/s-2007-968460
DOI: 10.1055/s-2007-968460
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Quaternary Carbon Stereocenters via NHC-Cu Induced Conjugate Addition
M. K. Brown, T. L. May, C. A. Baxter, A. H. Hoveyda*
Boston College, Chestnut Hill, USA
Further Information
Publication History
Publication Date:
24 April 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200705/lookinside/thumbnails/10.1055-s-2007-968460-1.jpg)
Significance
A new chiral N-heterocyclic carbene (NHC) promotes the Cu-catalyzed conjugate addition of alkylzinc reagents to cyclic γ-keto esters. This system accommodates sterically congested electrophilic sites to yield products containing quaternary carbon centers in significantly higher yields and ee values than previously reported systems. Further, selective in situ reduction of the ester moiety of the product conveniently affords chiral material amenable to further manipulation.