Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)‐Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures |
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| Authors: | Dr Huiling Jiang Dr Kai Lang Prof?Dr Hongjian Lu Dr Lukasz Wojtas Prof?Dr X Peter Zhang |
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| Institution: | 1. Department of Chemistry, University of South Florida, Tampa, FL, USA;2. Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts, USA;3. The Institute of Chemistry & Biomedical Sciences, Nanjing University, Nanjing, P.R. China |
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| Abstract: | Cobalt(II)‐based metalloradical catalysis (MRC) has been successfully applied for effective construction of the highly strained 2‐sulfonyl‐1,3‐diazabicyclo3.1.0]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. |
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| Keywords: | aziridination cobalt heterocycles metalloradical catalysis radicals |
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