Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)-Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures

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• 作者：Dr. Huiling Jiang ; Dr. Kai Lang ; Prof. Dr. Hongjian Lu ; Dr. Lukasz Wojtas and Prof. Dr. X. Peter Zhang
• 刊名：Angewandte Chemie International Edition
• 出版年：2016
• 出版时间：September 12, 2016
• 年：2016
• 卷：55
• 期：38
• 页码：11604-11608
• 全文大小：1100K
• ISSN：1521-3773

文摘

Cobalt(II)-based metalloradical catalysis (MRC) has been successfully applied for effective construction of the highly strained 2-sulfonyl-1,3-diazabicyclo[3.1.0]hexane structures in high yields through intramolecular radical aziridination of allylic sulfamoyl azides. The resulting [3.1.0] bicyclic aziridines prove to be versatile synthons for the preparation of a diverse range of 1,2- and 1,3-diamine derivatives by selective ring-opening reactions. As a demonstration of its application for target synthesis, the metalloradical intramolecular aziridination reaction has been incorporated as a key step for efficient synthesis of a potent neurokinin 1 (NK₁) antagonist in 60 % overall yield.