Dynamic Kinetic Asymmetric Synthesis of Substituted Pyrrolidines from Racemic Cyclopropanes and Aldimines: Reaction Development and Mechanistic Insights

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• 作者：Andrew T. Parsons ; Austin G. Smith ; Andrew J. Neel ; Jeffrey S. Johnson
• 刊名：Journal of the American Chemical Society
• 出版年：2010
• 出版时间：July 21, 2010
• 年：2010
• 卷：132
• 期：28
• 页码：9688-9692
• 全文大小：411K
• 年卷期：v.132,no.28(July 21, 2010)
• ISSN：1520-5126

文摘

An enantioselective preparation of 2,5-cis-disubstituted pyrrolidines has been achieved via a dynamic kinetic asymmetric transformation (DyKAT) of racemic donor−acceptor cyclopropanes and (E)-aldimines. Mechanistic studies suggest that isomerization of the aldimine or resultant iminium to the Z geometry is not a pathway that furnishes the observed 2,5-cis-disubstituted products.