Document Type

Article

Publication Date

6-4-2014

Keywords

asymmetric aziridination, aziridine, chiral porphyrin, cobalt complex, metalloradical catalysis, organophosphorus, phosphoryl azide

Digital Object Identifier (DOI)

http://dx.doi.org/10.3762/bjoc.10.129

Abstract

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

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