Pd-Catalyzed Enantioselective Three-Component Carboamination of 1,3-Cyclohexadiene

被引:0
|
作者
Wang, Jinrong [1 ]
Xu, Bing [1 ,2 ]
Wang, Yibo [3 ]
Xia, Guangzhen [4 ]
Zhang, Zhan-Ming [1 ,5 ]
Zhang, Junliang [1 ,2 ,6 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai 200438, Peoples R China
[2] Zhuhai Fudan Innovat Inst, Zhuhai 519000, Guangdong, Peoples R China
[3] Changchun Univ Technol, Adv Inst Mat Sci, Coll Chem & Life Sci, Changchun 130012, Jilin, Peoples R China
[4] Soochow Univ, Coll Chem, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Jiangsu, Peoples R China
[5] Fudan Zhangjiang Inst, Shanghai 201203, Peoples R China
[6] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
基金
国家重点研发计划; 中国博士后科学基金;
关键词
FUNCTIONALLY-SUBSTITUTED ARYL; ASYMMETRIC-SYNTHESIS; CONJUGATED DIENES; HECK/TSUJI-TROST; PALLADIUM; HETEROANNULATION; 1,3-DIENES; CAPTURE; ALLENES; CARBOANNULATION;
D O I
10.1021/jacs.4c07382
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric Pd-catalyzed three-component carboamination reactions of dienes to construct chiral cyclohexenylamines, which are of great importance in many fields of chemistry, have remained largely unexplored. Here, we demonstrate a highly enantio- and regioselective Pd/Ming-Phos-catalyzed carboamination reactions of 1,3-cyclohexadiene with readily available aryl iodides and anilines for facile access to diverse valuable chiral cyclohexenylamines. The process shows excellent functional group tolerance, easy scalability, and mild conditions. Moreover, mechanistic studies suggest that this reaction has a first-order dependence on the concentration of the palladium catalyst and aniline.
引用
收藏
页码:21231 / 21238
页数:8
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