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- Title
Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABA B Receptor.
- Authors
Shim, Jae Ho; Hong, Yeonsun; Kim, Ji Hae; Kim, Hyeon Soo; Ha, Deok-Chan
- 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.
- Subjects
GABA receptors; ENANTIOMERIC purity; CATALYTIC activity; CATALYSTS; HYDROPHOBIC interactions; NITROALKENES
- Publication
Catalysts (2073-4344), 2021, Vol 11, Issue 9, p1134
- ISSN
2073-4344
- Publication type
Article
- DOI
10.3390/catal11091134