title: Dynamic kinetic asymmetric synthesis of substituted pyrrolidines from racemic cyclopropanes and aldimines: reaction development and mechanistic insights.
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.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Andrew T
authors.initials: AT
authors.lastname: Parsons
authors.forename: Austin G
authors.initials: AG
authors.lastname: Smith
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Neel
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D011759:Pyrrolidines