Regiodivergent and Enantioselective Allylic C-H Alkylation of Allyl Ethers: Optimization, Scope, Mechanism and Application

被引：0

作者：

Wang, Hongkai ^{[1
]}

Song, Lijuan ^{[3
]}

Huang, Jing ^{[1
,4
]}

Wu, Fule ^{[1
]}

Yang, Zhuang ^{[5
,6
]}

Liu, Yangbin ^{[1
,4
]}

Wu, Yun-Dong ^{[1
,4
]}

Feng, Xiaoming ^{[1
,2
]}

机构：

[1] Inst Chem Biol, Shenzhen Bay Lab, Shenzhen 518132, Peoples R China

[2] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China

[3] Harbin Inst Technol Shenzhen, Sch Sci, Shenzhen 518055, Peoples R China

[4] Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncogen, Lab Computat Chem & Drug Design, Shenzhen 518055, Peoples R China

[5] Sichuan Univ, West China Hosp, Natl Clin Res Ctr Geriatr, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

[6] Sichuan Univ, West China Hosp, Canc Ctr, Natl Clin Res Ctr Geriatr, Chengdu 610041, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2025年

基金：

中国国家自然科学基金;

关键词：

regiodivergence; allylic C-H alkylation; vinyl ethers; allyl ethers; rocaglaol analogues; BOND FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; TERMINAL OLEFINS; ACTIVATION; ACID; OXIDATION; LIGANDS; PYRAZOL-5-ONES; CYCLOADDITION; CYCLIZATION;

D O I：

10.1002/anie.202500125

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Vinyl ethers and allyl ethers are important motifs in natural products and pharmaceuticals. Among various methods toward their synthesis, direct allylic C-H functionalization of allyl ethers is one of the most efficient approaches. In this study, one of two regioisomers, a vinyl ether or an allyl ether, could be obtained, depending on whether a Lewis acid co-catalyst was present. Furthermore, branched allyl ethers were smoothly prepared in excellent regio- and enantioselectivity (up to 20 : 1 b/l, 99 % ee) by synergistic catalysis with an achiral Pd(0) complex and a chiral Lewis acid catalyst.

引用

页数：13