asymmetric aziridination, aziridine, chiral porphyrin, cobalt complex, metalloradical catalysis, organophosphorus, phosphoryl azide
Digital Object Identifier (DOI)
The Co(II) complex of a new D2-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.
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Citation / Publisher Attribution
Beilstein Journal of Organic Chemistry, v. 10, p. 1282-1289
Scholar Commons Citation
Tao, Jingran; Jin, Li-Mei; and Zhang, X. Peter, "Synthesis of Chiral N-Phosphoryl Aziridines Through Enantioselective Aziridination of Alkenes with Phosphoryl Azide via Co(II)-Based Metalloradical Catalysis" (2014). Chemistry Faculty Publications. Paper 14.