Catalytic Generation of Activated Carboxylates:  Direct, Stereoselective Synthesis of β-Hydroxyesters from Epoxyaldehydes

Kenneth Yu-Kin Chow and Jeffrey W. Bode*
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510
J. Am. Chem. Soc., 2004, 126 (26), pp 8126–8127
DOI: 10.1021/ja047407e
Publication Date (Web): June 15, 2004
Copyright © 2004 American Chemical Society
*

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

, bode@chem.ucsb.edu

Abstract

Abstract Image

The catalytic generation of activated carboxylates from epoxyaldehydes enables the direct, stereoselective synthesis of β-hydroxyesters under mild, convenient reaction conditions. In addition to providing a new method for the synthesis of anti-aldol adducts, this chemistry unveils a mechanistically viable solution to the catalytic, waste-free synthesis of esters.

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History

  • Published In Issue July 07, 2004
  • Received May 3, 2004

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