Organocatalytic asymmetric michael addition in aqueous media by a hydrogen-bonding catalyst and application for inhibitors of gabab receptor

Jae Ho Shim, Yeonsun Hong, Ji Hae Kim, Hyeon Soo Kim, Deok Chan Ha

Research output: Contribution to journalArticlepeer-review

Abstract

Catalysts based on (R, R)-1,2-diphenylethylenediamine are, as chiral organic catalysts, applied to the asymmetric Michael addition to α, β-unsaturated nitroalkenes under neutral conditions. The role of an aqueous medium for organic catalytic activity can be reversed concerning hydrophilic-hydrophobic function depending on the reaction conditions. In this study, to provide an environmentally friendly system, the thiourea-based catalyst substituted with 3,5-(CF3 )2-Ph was used in water solvents. The hydrophobic effect of the substituent provided fast reaction, high chemical yield, and mirror-image selectivity. This reaction allowed the preparation of GABAB agonists in an optically pure manner. Additionally, GABA (γ-aminobutyric acid) analogs such as baclofen and phenibut were synthesized as R-type S-type with high optical purity.

Original languageEnglish
Article number1134
JournalCatalysts
Volume11
Issue number9
DOIs
Publication statusPublished - 2021 Sep

Keywords

  • Calcium release
  • Inhibitor of GABA receptor
  • Michael addition
  • Organic chemistry

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

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