Catalytic Asymmetric Rearrangement of Allylic Trichloroacetimidates. A Practical Method for Preparing Allylic Amines and Congeners of High Enantiomeric Purity

Carolyn E. Anderson and Larry E. Overman*
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025
J. Am. Chem. Soc., 2003, 125 (41), pp 12412–12413
DOI: 10.1021/ja037086r
Publication Date (Web): September 19, 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.

, leoverma@uci.edu

Abstract

Abstract Image

COP−Cl catalyzes the rearrangement of (E)-allylic trichloroacetimidates to provide transposed allylic trichloroacetamides of high enantiopurity, a transformation that underlies the first truly practical method for transforming prochiral allylic alcohols to enantioenriched allylic amines and congeners. The high functional group compatibility of this asymmetric rearrangement and the demonstrated broad utility in synthesis of the allylic trichloroacetimidate to allylic trichloroacetamide conversion are singular features of this new catalytic asymmetric reaction.

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History

  • Published In Issue October 15, 2003
  • Received July 5, 2003

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