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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, Email: gcfmit.edu

E. C. Lee, B. L. Hodous, E. Bergin, C. Shih, G. C. Fu, J. Am. Chem. Soc., 2005, 127, 11586-11587.

DOI: 10.1021/ja052058p (free Supporting Information)


Abstract

A catalytic enantioselective Staudinger reactions is described that preferentially furnish trans β-lactams. The use of an N-triflyl protecting group for the imine is crucial for the success of the reaction.

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Enantioselective Staudinger Synthesis of β-Lactams Catalyzed by a Planar-Chiral Nucleophile

B. L. Hodous, G. C. Fu, J. Am. Chem. Soc., 2002, 124, 1578-1579.


Key Words

β-Lactams, Staudinger Synthesis


ID: J48-Y2005-2550