title: Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis.
abstract: The Co(II) complex of a new D 2-symmetric chiral porphyrin 3,5-DiMes-QingPhyrin, [Co(P6)], can catalyze asymmetric aziridination of alkenes with bis(2,2,2-trichloroethyl)phosphoryl azide (TcepN3) as a nitrene source. This new Co(II)-based metalloradical aziridination is suitable for different aromatic olefins, producing the corresponding N-phosphorylaziridines in good to excellent yields (up to 99%) with moderate to high enantioselectivities (up to 85% ee). In addition to mild reaction conditions and generation of N2 as the only byproduct, this new metalloradical catalytic system is highlighted with a practical protocol that operates under neutral and non-oxidative conditions.
authors.affiliation: Department of Chemistry, University of South Florida, Tampa, Florida 33620, USA.
authors.forename: Jingran
authors.initials: J
authors.lastname: Tao
authors.affiliation: Department of Chemistry, University of South Florida, Tampa, Florida 33620, USA.
authors.forename: Li-Mei
authors.initials: LM
authors.lastname: Jin
authors.affiliation: Department of Chemistry, University of South Florida, Tampa, Florida 33620, USA.
authors.forename: X Peter
authors.initials: XP
authors.lastname: Zhang
keywords: asymmetric aziridination; aziridine; chiral porphyrin; cobalt complex; metalloradical catalysis; organophosphorus; phosphoryl azide