A Practical Method for Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers through NHC-Cu-Catalyzed Conjugate Additions of Alkyl- and Arylzinc Reagents to β-Substituted Cyclic Enones
Kang-sang Lee, M. Kevin Brown, Alexander W. Hird and Amir H. Hoveyda*
*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut
Hill, Massachusetts 02467, Email: amir.hoveyda
bc.edu
K.-S. Lee, M. K. Brown, A. W. Hird, A. H. Hoveyda, J. Am. Chem. Soc., 2006, 128, 7182-7184.
DOI: 10.1021/ja062061o (free Supporting Information)
Abstract
Cu-catalyzed enantioselective conjugate additions of alkyl- and arylzinc reagents to unactivated cyclic β-substituted enones are promoted in the presence of 2.5-15 mol% of a readily available chiral NHC-based Cu complex, affording the desired products bearing all-carbon quaternary stereogenic centers in good yield and enantioselectivity.
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ID: J48-Y2006-2120
