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

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 = relationshi...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-08, Vol.127 (33), p.11586-11587
Main Authors: Lee, Elaine C, Hodous, Brian L, Bergin, Enda, Shih, Crystal, Fu, Gregory C
Format: Article
Language:English
Subjects:
beta-Lactams - chemical synthesis
Catalysis
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Molecular Structure
Nitrogen - chemistry
Organic chemistry
Oxidation-Reduction
Reactivity and mechanisms
Stereoisomerism
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Summary: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 R). 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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja052058p