Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes

被引：22
作者：
Ye, Yang [1 ,2 ]
Liu, Jiandong [3 ]
Xu, Bing [1 ,2 ]
Jiang, Songwei [1 ,2 ]
Bai, Renren [1 ,2 ]
Li, Shijun [4 ]
Xie, Tian [1 ,2 ]
Ye, Xiang-Yang [1 ,2 ]
机构：
[1] Hangzhou Normal Univ, Sch Pharm, Hangzhou 311121, Zhejiang, Peoples R China
[2] Hangzhou Normal Univ, Collaborat Innovat Ctr Tradit Chinese Med Zhejian, Key Lab Elemene Class Anticanc Chinese Med, Engn Lab Dev & Applicat Tradit Chinese Med, Hangzhou 311121, Zhejiang, Peoples R China
[3] Shanghai Univ, Ctr Supramol Chem & Catalysis, Dept Chem, Shanghai 200444, Peoples R China
[4] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 311121, Zhejiang, Peoples R China
来源：
CHEMICAL SCIENCE | 2021年 / 12卷 / 39期
基金：
中国国家自然科学基金;
关键词：
COPPER(I)-CATALYZED REACTION; ARYLBORATION; PALLADIUM; VINYL; CARBOBORATION; HALIDES; FUNCTIONALIZATION; ACTIVATION; SECONDARY; ALKENES;
D O I：
10.1039/d1sc04071e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel nickel-catalyzed asymmetric 1,2-vinylboration reaction has been developed to afford benzylic alkenylboration products with high yields and excellent enantioselectivities by using a chiral bisoxazoline ligand. Under optimized conditions, a wide variety of chiral 2-boryl-1,1-arylvinylalkanes are efficiently prepared from readily available olefins and vinyl halides in the presence of bis(pinacolato)diboron as the boron source in a mild and easy-to-operate manner. This three-component cascade protocol furnishes exceptional chemo- and stereoselectivity, and its usefulness is illustrated by its application in asymmetric modifications of several structurally complex natural products and pharmaceuticals.
引用
收藏
页码：13209 / 13215
页数：7
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