title: Diastereoselective aziridination of chiral electron-deficient olefins with N-chloro-N-sodiocarbamates catalyzed by chiral quaternary ammonium salts.
abstract: Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the "matching" stereochemical combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,5,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Murakami
authors.forename: Youhei
authors.initials: Y
authors.lastname: Takeda
authors.forename: Satoshi
authors.initials: S
authors.lastname: Minakata
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001388:Aziridines; D000644:Quaternary Ammonium Compounds