Stereoselective radical C–H alkylation with acceptor/acceptor-substituted diazo reagents via Co(II)-based metalloradical catalysis

Authors

Xin Cui, CUNY Bernard M Baruch CollegeFollow
Xue Xu, University of South Florida
Li-Men Jin, University of South Florida
Lukasz Wojtas, University of South Florida
X. Peter Zhang, University of South Florida

Document Type

Article

Publication Date

2015

Abstract

Co(II)-based metalloradical catalysis has, for the first time, been successfully applied for asymmetric intramolecular C–H alkylation of acceptor/acceptor-substituted diazo reagents. Through the design and synthesis of a new D₂-symmetric chiral amidoporphyrin as the supporting ligand, the Co(II)-based metalloradical system, which operates at room temperature, is capable of 1,5-C–H alkylation of α-methoxycarbonyl-α-diazosulfones with a broad range of electronic properties, providing the 5-membered sulfolane derivatives in high yields with excellent diastereoselectivities and enantioselectivities. In addition to complete chemoselectivity toward allylic and allenic C–H bonds, the Co(II)-based metalloradical catalysis for asymmetric C–H alkylation features a remarkable degree of functional group tolerance.

Comments

This article was originally published in Chemical Science, available at DOI: 10.1039/c4sc02610a .

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.