Nickel-Catalyzed 1,2-Carboamination of Alkenyl Alcohols

被引：59
|
作者：
Kang, Taeho [1 ]
Kim, Nana [1 ]
Cheng, Peter T. [2 ]
Zhang, Hao [2 ]
Foo, Klement [2 ]
Engle, Keary M. [1 ]
机构：
[1] Scripps Res, Dept Chem, La Jolla, CA 92037 USA
[2] Bristol Myers Squibb Res & Early Dev, Discovery Chem, Princeton, NJ 08543 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 34期
基金：
美国国家科学基金会;
关键词：
3-COMPONENT CARBOAMINATION; ELECTROPHILIC AMINATION; SYN-CARBOAMINATION; HYDROAMINATION; CARBOALKOXYLATION; CONSTRUCTION; DERIVATIVES; ACCESS; ARYL;
D O I：
10.1021/jacs.1c07112
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An alcohol-directed, nickel-catalyzed three-component umpolung carboamination of unactivated alkenes with aryl/alkenylboronic esters and electrophilic aminating reagents is reported. This transformation is enabled by specifically tailored O-(2,6-dimethoxybenzoyOhydroxylamine electrophiles that suppress competitive processes, including undesired beta-hydride elimination and transesterification between the alcohol substrate and electrophile. The reaction delivers the desired 1,2-carboaminated products with generally high regio- and syn-diastereoselectivity and exhibits a broad scope of coupling partners and alkenes, including complex natural products. Various mechanistic experiments and analysis of the stereochemical outcome with a cyclic alkene substrate, as confirmed by X-ray crystallographic analysis, support alcohol-directed svn-insertion of an organonickel(I) species.
引用
收藏
页码：13962 / 13970
页数：9
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