Synthesis of Chiral Vicinal Diamines by Silver(I)-Catalyzed Enantioselective Aminolysis of N-Tosylaziridines

Abstract

The kinetic resolution of 2-aryl-N-tosylaziridines and the asymmetric desymmetrization of meso-N-tosylaziridines by ring openings with various primary and secondary anilines, and aliphatic amines as nucleophile have been realized by using a single silver(I)/chiral diphosphine complex as catalyst for the first time. The simple starting materials, broad scope, and easy scalability render this protocol a practical way to chiral vicinal diamine derivatives.

Keywords: amines; aziridines; desymmetrization; kinetic resolution; silver.