Catalytic Asymmetric Staudinger Reactions to Form -Lactams: An Unanticipated Dependence of Diastereoselectivity on th

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• 作者：Elaine C. Lee ; Brian L. Hodous ; Enda Bergin ; Crystal Shih ; and Gregory C. Fu
• 刊名：Journal of the American Chemical Society
• 出版年：2005
• 出版时间：August 24, 2005
• 年：2005
• 卷：127
• 期：33
• 页码：11586 - 11587
• 全文大小：54K
• 年卷期：v.127,no.33(August 24, 2005)
• ISSN：1520-5126

文摘

There are relatively few methods for the catalytic asymmetric synthesis of mages/gifchars/beta2.gif" BORDER=0 ALIGN="middle">-lactams, and those that have been reported are generally cis selective. This communication describes the first catalytic enantioselective Staudinger reactions that preferentially furnish trans mages/gifchars/beta2.gif" BORDER=0 ALIGN="middle">-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 mages/gifchars/beta2.gif" BORDER=0 ALIGN="middle">-lactams readily react with nucleophiles to generate useful families of compounds, such as mages/gifchars/gamma.gif" BORDER=0 >-amino alcohols and mages/gifchars/beta2.gif" BORDER=0 ALIGN="middle">-amino acids.