Catalytic Radical Process for Enantioselective Amination of C(sp³)−H Bonds

Authors

Chaoqun Li, University of South Florida
Kai Lang, Boston College
Hongjian Lu, University of South Florida
Yang Hu, University of South Florida
Xin Cui, University of South Florida
Lukasz Wojtas, University of South FloridaFollow
X. P. Zhang, Boston College

Document Type

Article

Publication Date

12-2018

Keywords

amines, cobalt, heterocycles, radicals, reaction mechanisms

Digital Object Identifier (DOI)

https://doi.org/10.1002/anie.201808923

Abstract

A new catalytic radical system involving CoII‐based metalloradical catalysis is effective in activating sulfamoyl azides for enantioselective radical 1,6‐amination of C(sp3)−H bonds, affording six‐membered chiral heterocyclic sulfamides in high yields with excellent enantioselectivities. The CoII‐catalyzed C−H amination features an unusual degree of functional‐group tolerance and chemoselectivity. The unique reactivity and stereoselectivity is attributed to the underlying stepwise radical pathway. The resulting optically active cyclic sulfamides can be readily converted into synthetically useful chiral 1,3‐diamine derivatives without loss in enantiopurity.

Was this content written or created while at USF?

Yes

Citation / Publisher Attribution

Angewandte Chemie International Edition, v. 57, issue 51, p. 16837-16841

Scholar Commons Citation

Li, Chaoqun; Lang, Kai; Lu, Hongjian; Hu, Yang; Cui, Xin; Wojtas, Lukasz; and Zhang, X. P., "Catalytic Radical Process for Enantioselective Amination of C(sp³)−H Bonds" (2018). Chemistry Faculty Publications. 53.
https://digitalcommons.usf.edu/chm_facpub/53