A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction

David A. Evans,* Daniel Seidel, Magnus Rueping, Hon Wai Lam, Jared T. Shaw, and C. Wade Downey
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138
J. Am. Chem. Soc., 2003, 125 (42), pp 12692–12693
DOI: 10.1021/ja0373871
Publication Date (Web): September 27, 2003
Copyright © 2003 American Chemical Society

Abstract

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A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87−94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.

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History

  • Published In Issue October 22, 2003
  • Received July 18, 2003

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