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. 2010 Jul 21;132(28):9688-92.
doi: 10.1021/ja1032277.

Dynamic kinetic asymmetric synthesis of substituted pyrrolidines from racemic cyclopropanes and aldimines: reaction development and mechanistic insights

Andrew T Parsons  1 , Austin G Smith, Andrew J Neel, Jeffrey S Johnson
Affiliations

Dynamic kinetic asymmetric synthesis of substituted pyrrolidines from racemic cyclopropanes and aldimines: reaction development and mechanistic insights

Andrew T Parsons et al. J Am Chem Soc. .

Abstract

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.

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