Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)‐Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures |
| |
Authors: | Dr. Huiling Jiang Dr. Kai Lang Prof. Dr. Hongjian Lu Dr. Lukasz Wojtas Prof. Dr. X. Peter Zhang |
| |
Affiliation: | 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 |
| |
Abstract: | 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. |
| |
Keywords: | aziridination cobalt heterocycles metalloradical catalysis radicals |
|
|