γ-Amino Butyric Acid (GABA) Synthesis Enabled by Copper-Catalyzed Carboamination of Alkenes

被引:57
|
作者
Zhu, Nengbo [1 ]
Wang, Ting [2 ]
Ge, Liang [1 ]
Li, Yajun [1 ]
Zhang, Xinhao [2 ]
Bao, Hongli [1 ]
机构
[1] Univ Chinese Acad Sci, State Key Lab Struct Chem, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, 155 Yangqiao Rd West, Fuzhou 350002, Fujian, Peoples R China
[2] Peking Univ, Shenzhen Grad Sch, Key Lab Chem Genom, Lab Computat Chem & Drug Design, Shenzhen 518055, Peoples R China
关键词
POLAR CROSSOVER REACTIONS; BOND-FORMING REACTIONS; FREE-RADICAL REACTIONS; C-H ACTIVATION; ALKYL NITRILES; ACETONITRILE; FUNCTIONALIZATION; PYRROLIDINE; MECHANISM; CASCADE;
D O I
10.1021/acs.orglett.7b01969
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
gamma-Amino butyric acid" (GABA) is the chief inhibitory neurotransmitter in the mammalian central nervous system. Many GABA derivatives are used clinically to prevent or treat neurodegenerative diseases. Copper-catalyzed carboamination of alkenes offers an efficient method to fashion the core structure of GABA derivatives from alkenes. In this reaction, acetonitrile serves as the source of the carbon and nitrogen functionalities used to difunctionalize alkenes. Experimental and density functional theory (DFT) studies were carried out to investigate the mechanism of the reaction, and a copper-catalyzed radical polar crossover mechanism is proposed.
引用
收藏
页码:4718 / 4721
页数:4
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