Photoinduced Copper-Catalyzed Asymmetric Three-Component Coupling of 1,3-Dienes: An Alternative to Kharasch-Sosnovsky Reaction

被引：129

作者：

Wang, Peng-Zi ^{[1
]}

Wu, Xue ^{[1
]}

Cheng, Ying ^{[1
]}

Jiang, Min ^{[2
]}

Xiao, Wen-Jing ^{[1
,3
]}

Chen, Jia-Rong ^{[1
,4
]}

机构：

[1] Cent China Normal Univ, CCNU uOttawa Joint Res Ctr, Key Lab Pesticides & Chem Biol, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China

[2] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310036, Peoples R China

[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[4] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 42期

关键词：

1; 3-dienes; asymmetric C-O coupling; copper catalysis; Kharasch-Sosnovsky-type reaction; photoredox catalysis; ALLYLIC OXIDATION; 1,2-DIFUNCTIONALIZATION; FUNCTIONALIZATION; BISOXAZOLINE; ALKENES; OLEFINS; PHOTOREDOX;

D O I：

10.1002/anie.202110084

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Kharasch-Sosnovsky reaction is one of the most powerful methods for allylic oxidation of alkenes. However, the inherent radical mechanism and use of peroxides as both oxidants and oxygen nucleophiles render dearth of universal catalytic systems for highly enantioselective variants and limited scope. Herein, an alternative to the asymmetric Kharasch-Sosnovsky reaction that utilized a chiral copper catalyst and purple-LED irradiation to enable the three-component coupling of 1,3-dienes, oxime esters, and carboxylic acids is reported. This protocol features mild conditions, remarkable scope and functional group tolerance as evidenced by >80 examples and utility in the late-stage modification of pharmaceuticals and natural products. Detailed mechanistic studies provide evidences for the radical-based reaction pathway.

引用

页码：22956 / 22962

页数：7

共 64 条

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