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

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posted on 01.09.2017, 18:53 by Nengbo Zhu, Ting Wang, Liang Ge, Yajun Li, Xinhao Zhang, Hongli Bao
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.