Asymmetric Mannich synthesis of α-amino esters by anion-binding catalysis.

ABSTRACT: We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively by generating an iminium ion by chloride abstraction and an enolate by deprotonation, followed by highly stereoselective C-C bond formation between both reactive intermediates associated non-covalently within the catalyst framework.

SUBMITTER: Wasa M 

PROVIDER: S-EPMC4183616 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature