Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes

被引：45

作者：

Lin, Zhiyang ^{[1
]}

Jin, Youxiang ^{[1
]}

Hu, Weitao ^{[1
]}

Wang, Chuan ^{[1
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Dept Chem, Ctr Excellence Mol Synth, 96 Jinzhai Rd, Hefei 20237, Anhui, Peoples R China

来源：

CHEMICAL SCIENCE | 2021年 / 12卷 / 19期

基金：

中国国家自然科学基金;

关键词：

This work is supported by 1000-Youth Talents Plan start up funding; the National Natural Science Foundation of China (21772183; 22071230); the Fundamental Research Funds for the Central Universities (WK2060190086) and the University of Science and Technology of China;

D O I：

10.1039/d1sc01115d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we report a nickel-catalyzed asymmetric reductive aryl-allylation of aryl iodide-tethered unactivated alkenes, wherein both acyclic allyl carbonates and cyclic vinyl ethylene carbonates can serve as the coupling partners. Furthermore, the direct use of allylic alcohols as the electrophilic allyl source in this reaction is also viable in the presence of BOC anhydride. Remarkably, this reaction proceeds with high linear/branched-, E/Z- and enantio-selectivity, allowing the synthesis of various chiral indanes and dihydrobenzofurans (50 examples) containing a homoallyl-substituted quaternary stereocenter with high optical purity (90-98% ee). In this reductive reaction, the use of pregenerated organometallics can be circumvented, giving this process good functionality tolerance and high step-economy.

引用

页码：6712 / 6718

页数：7