Affiliation:
1. Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction College of Chemistry Central China Normal University 152 Luoyu Road Wuhan Hubei 430079 China
2. College of Materials Chemistry and Chemical Engineering Hangzhou Normal University Hangzhou 310036 China
3. Wuhan Institute of Photochemistry and Technology 7 North Bingang Road Wuhan Hubei 430083 China
4. Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province Gannan Normal University Ganzhou Jiangxi 341000 China
Abstract
AbstractRadical‐involved multicomponent difunctionalization of 1,3‐dienes has recently emerged as a promising strategy for rapid synthesis of valuable allylic compounds in one‐pot operation. However, the expansion of radical scope and enantiocontrol remain two major challenges. Herein, we describe an unprecedented photoinduced copper‐catalyzed highly enantioselective three‐component radical 1,2‐azidooxygenation of 1,3‐dienes with readily available azidobenziodazolone reagent and carboxylic acids. This mild protocol exhibits a broad substrate scope, high functional group tolerance, and exceptional control over chemo‐, regio‐ and enantioselectivity, providing practical access to diverse valuable azidated chiral allylic esters. Mechanistic studies imply that the chiral copper complex is implicated as a bifunctional catalyst in both the photoredox catalyzed azidyl radical generation and enantioselective radical C−O cross‐coupling.
Funder
National Natural Science Foundation of China