Design of Chiral N-Triflyl Phosphoramide as a Strong Chiral Brønsted Acid and Its Application to Asymmetric Diels−Alder Reaction

Daisuke Nakashima and Hisashi Yamamoto*
Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637
J. Am. Chem. Soc., 2006, 128 (30), pp 9626–9627
DOI: 10.1021/ja062508t
Publication Date (Web): July 6, 2006
Copyright © 2006 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.

, yamamoto@uchicago.edu

Abstract

Abstract Image

A highly reactive and acidic chiral Brønsted acid catalyst, chiral N-triflyl phosphoramide, was developed. Highly enantioselective Diels−Alder reaction of α,β-unsaturated ketone with silyloxydiene was demonstrated using this chiral Brønsted acid catalyst.

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History

  • Published In Issue August 02, 2006
  • Received April 19, 2006

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