title: Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)-Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures.
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.
authors: Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA.
authors: Huiling
authors: H
authors: Jiang
authors: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts, 02467, USA.
authors: Kai
authors: K
authors: Lang
authors: Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA.|The Institute of Chemistry & Biomedical Sciences, Nanjing University, Nanjing, 210093, P.R. China.
authors: Hongjian
authors: H
authors: Lu
authors: Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA.
authors: Lukasz
authors: L
authors: Wojtas
authors: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts, 02467, USA. peter.zhang@bc.edu.|Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA. peter.zhang@bc.edu.
authors: X Peter
authors: XP
authors: Zhang
mesh_terms: D001386:Azides / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D064729:Neurokinin-1 Receptor Antagonists / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D001386:Azides; D001388:Aziridines; D001643:Bridged Bicyclo Compounds; D056831:Coordination Complexes; D064729:Neurokinin-1 Receptor Antagonists; D003035:Cobalt
keywords: aziridination; cobalt; heterocycles; metalloradical catalysis; radicals