3 years ago

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

γ-Amino Butyric Acid (GABA) Synthesis Enabled by Copper-Catalyzed Carboamination of Alkenes
Xinhao Zhang, Yajun Li, Liang Ge, Ting Wang, Hongli Bao, Nengbo Zhu
γ-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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01969

DOI: 10.1021/acs.orglett.7b01969

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