Catalytic asymmetric kinetic resolution of 2-ethynylaziridines via nucleophilic ring opening with amines

Abstract

The enantioselective kinetic resolution of racemic 2-ethynylaziridines via ring opening with amines is realized under the catalysis of a chiral Cu(I)–bisphosphine combination. This protocol provides an expedient way to access synthetically valuable enantioenriched propargylic vicinal diamines (70%–95% yields, 14%–95% ee) and 2-ethynylaziridines (70%–95% recovery rates, 14%–95% ee) within 15–240 h under mild reaction conditions.