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

Supporting Info

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

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, evans@chemistry.harvard.edu

Abstract

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

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Communication

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