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: gcf
mit.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
Abstract
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.
see article for more examples
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
