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

Zhuo Chai; Pei-Jun Yang; Hu Zhang; Shaowu Wang; Gaosheng Yang

doi:10.1002/anie.201610693

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

Angew Chem Int Ed Engl. 2017 Jan 9;56(2):650-654. doi: 10.1002/anie.201610693. Epub 2016 Dec 5.

Authors

Zhuo Chai¹, Pei-Jun Yang¹, Hu Zhang¹, Shaowu Wang^{1

2}, Gaosheng Yang¹

Affiliations

¹ Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, 1 East Beijing Road, Wuhu, Anhui, 241000, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P.R. China.

PMID: 27918132
DOI: 10.1002/anie.201610693

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.

Publication types

Research Support, Non-U.S. Gov't