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

被引：233

作者：

Parsons, Andrew T. ^{[1
]}

Smith, Austin G. ^{[1
]}

Neel, Andrew J. ^{[1
]}

Johnson, Jeffrey S. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 28期

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; RING-EXPANSION REACTION; DIASTEREOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITION; NITRONES; TETRAHYDROFURANS; DERIVATIVES; ALDEHYDES; CONSTRUCTION;

D O I：

10.1021/ja1032277

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：9688 / 9692

页数：5

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