Kinetic Resolution of Aziridines via Catalytic Asymmetric Ring-Opening Reaction with Mercaptobenzothiazoles.

Abstract

A highly efficient kinetic resolution of racemic 2-acyl-3-aryl-N-tosylaziridines is achieved through a chiral Lewis acid promoted ring-opening reaction with 2-mercaptobenzothiazoles as the nucleophiles. The chiral N,N'-dioxide-lanthanum complex as catalyst and the 2-mercaptobenzothiazoles as active sulfur nucleophiles are the keys to the success of the reaction. A variety of enantioenriched β-amino thioethers and aziridines are obtained in good yields with good ee values.