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

• Published in: Angewandte Chemie International Edition Vol. 56; no. 2; pp. 650 - 654
• Main Authors: Chai, Zhuo, Yang, Pei‐Jun, Zhang, Hu, Wang, Shaowu, Yang, Gaosheng
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 09-01-2017
• Edition: International ed. in English
• Subjects: Aliphatic amines; Amines; Aromatic compounds; aziridines; Chemical synthesis; desymmetrization; Diamines; Enantiomers; kinetic resolution; Silver; amines; kinetic resolution; aziridines; silver; desymmetrization
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201610693

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.
Two birds, one stone: The nucleophilic ring opening of N‐tosylaziridines by various primary and secondary aromatic and aliphatic amines for both racemic aziridines (by kinetic resolution) and meso‐aziridines (by desymmetrization) has been realized by using a single silver(I)/chiral diphosphine complex. The method provides practical and efficient access to a variety of useful chiral vicinal diamines.