Catalytic Asymmetric Staudinger Reactions to Form β-Lactams:  An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent

Elaine C. Lee, Brian L. Hodous, Enda Bergin, Crystal Shih, and Gregory C. Fu*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2005, 127 (33), pp 11586–11587
DOI: 10.1021/ja052058p
Publication Date (Web): July 30, 2005
Copyright © 2005 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.

, gcf@mit.edu

Abstract

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There are relatively few methods for the catalytic asymmetric synthesis of β-lactams, and those that have been reported are generally cis selective. This communication describes the first catalytic enantioselective Staudinger reactions that preferentially furnish trans β-lactams (trans = relationship of Ph to R1). The key to this method is the use of an N-triflyl protecting group for the imine. Along with serving as interesting targets in their own right, N-triflyl β-lactams readily react with nucleophiles to generate useful families of compounds, such as γ-amino alcohols and β-amino acids.

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History

  • Published In Issue August 24, 2005
  • Received March 31, 2005

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