Formation of scalemic aziridines via the nucleophilic opening of aziridines

A novel method for the preparation of enantiomerically pure monosubstituted aziridines was developed based on the reaction of an aziridine tosylate with a primary organocuprate reagent. The synthetic strategy was characterized by the formation of ring-opened intermediates due to the attack of cuprate to the least-substituted carbon of the aziridine ring. Subsequent ring closure of the intermediates via displacement of the tosyl ester in the presence of chiral solvating agents led to the formation of the aziridines.