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An Efficient Synthesis of Enantiomerically Pure γ-Aminobutyric Acid (GABA) Derivatives
Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
- 1 Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
- 2 Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
- 3 Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
- 4 Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
- 5 Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi’an, China
Journal of Materials Science and Chemical Engineering·Volume 05 (2017)·Pages 25–32·Published 11 August 2017·DOI10.4236/msce.2017.58003
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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.
KeywordsChiralGABAOrganocatalystAsymmetric Michael Addition
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