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)
A catalytic enantioselective Staudinger reaction is described that preferentially furnishes 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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B. L. Hodous, G. C. Fu, J. Am. Chem. Soc., 2002, 124, 1578-1579.