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
J. Am. Chem. Soc., 2002, 124 (28), pp 8192–8193
DOI: 10.1021/ja020605q
Publication Date (Web): June 19, 2002
Copyright © 2002 American Chemical Society
*

 To whom correspondence should be addressed. E-mail:  amir.hoveyda@bc.edu.

Abstract

Abstract Image

An efficient and highly enantioselective (≥92% ee) catalytic method for conjugate addition of alkylzinc reagents to cyclic nitroalkenes is reported. Reactions are 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. The Cu-catalyzed reactions can be effectively carried out with small-, medium-, and large-ring nitroalkenes. Depending on the reaction conditions used, either the nitro or the corresponding α-substituted ketone product can be readily accessed by the present protocol.

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History

  • Published In Issue July 17, 2002
  • Received April 26, 2002

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