Polarizing the Nazarov Cyclization:  Efficient Catalysis under Mild Conditions

Wei He, Xiufeng Sun, and Alison J. Frontier*
Department of Chemistry, University of Rochester, Rochester, New York 14627
J. Am. Chem. Soc., 2003, 125 (47), pp 14278–14279
DOI: 10.1021/ja037910b
Publication Date (Web): October 30, 2003
Copyright © 2003 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.

, frontier@chem.rochester.edu

Abstract

Abstract Image

Substituted divinyl ketones were studied in the Nazarov cyclization. α-Carbomethoxy divinyl ketones underwent efficient Nazarov cyclization with catalytic copper triflate (2 mol %) to give a single cyclopentenone regio- and stereoisomer. The efficiency of the cyclizations correlated with the ability of the substituents to favorably polarize the π-system of the cationic intermediate.

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History

  • Published In Issue November 26, 2003
  • Received August 13, 2003

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