Synthesis of Chiral N-Phosphoryl Aziridines Through Enantioselective Aziridination of Alkenes with Phosphoryl Azide via Co(II)-Based Metalloradical Catalysis

Authors

Jingran Tao, University of South Florida
Li-Mei Jin, University of South Florida
X. Peter Zhang, University of South FloridaFollow

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.

Rights Information

This work is licensed under a Creative Commons Attribution 3.0 License.

Was this content written or created while at USF?

Yes

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. 14.
https://digitalcommons.usf.edu/chm_facpub/14