Cu-Catalyzed Enantioselective Conjugate Addition of Alkylzincs to Cyclic Nitroalkenes: Catalytic Asymmetric Synthesis of Cyclic α-Substituted Ketones

Courtney A. Luchaco-Cullis and Amir H. Hoveyda*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, Email: amir.hoveydabc.edu

C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 8192-8193.

DOI: 10.1021/ja020605q

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Abstract

An efficient and highly enantioselective conjugate addition of alkylzinc reagents to various cyclic nitroalkenes is promoted in the presence of 0.5-5 mol % (CuOTf)₂·C₆H₆ and 1-10 mol % of chiral amino acid-based phosphine ligands at 0°C in toluene. Depending on the reaction conditions used, either the nitro or the corresponding α-substituted ketone product can be accessed.

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Key Words

nitro compounds, Nef Reaction, α-substituted ketones

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ID: J48-Y2002-1210