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

Andrew T Parsons; Austin G Smith; Andrew J Neel; Jeffrey S Johnson

doi:10.1021/ja1032277

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

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

Authors

Andrew T Parsons¹, Austin G Smith, Andrew J Neel, Jeffrey S Johnson

Affiliation

¹ Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.

PMID: 20572661
DOI: 10.1021/ja1032277

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Cyclopropanes / chemistry*
Kinetics
Magnetic Resonance Spectroscopy
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Stereoisomerism

Substances

Cyclopropanes
Pyrrolidines