TITLE:
An Efficient Synthesis of Enantiomerically Pure γ-Aminobutyric Acid (GABA) Derivatives
AUTHORS:
Huixia Liu, Jiani Yuan, Qinqin Tian, Nan Ji, Wei He
KEYWORDS:
Chiral, GABA, Organocatalyst, Asymmetric Michael Addition
JOURNAL NAME:
Journal of Materials Science and Chemical Engineering,
Vol.5 No.8,
August
11,
2017
ABSTRACT:
Chiral γ-aminobutyric acid (GABA) derivatives are the normal inhibitory neurotransmitters in the mammalian central nervous system. In this paper, enantiopure GABA derivatives 6 were synthesized via reduction/cyclization/hydrolysis cascade reactions from the highly enantioselective β-aryl-γ- ni-troalkanes Michael adducts 4, which was obtained from asymmetric Michael addition of S, S’-diphenyldithiomalonate 2 to trans-β-nitroolefins 1, using novel chiral cinchona alkaloid-derived thioureas 3 as the organocatalysts. This synthesis represents an efficient, highly selective and environmental benign methodology for GABA derivatives.