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
- Issue Date
- Sep-2021
- Publisher
- Multidisciplinary Digital Publishing Institute (MDPI)
- Keywords
- Michael addition; inhibitor of GABA(B) receptor; organic chemistry; calcium release
- Citation
- Catalysts, v.11, no.9
- Indexed
- SCIE
SCOPUS
- Journal Title
- Catalysts
- Volume
- 11
- Number
- 9
- URI
- https://scholarworks.korea.ac.kr/kumedicine/handle/2020.sw.kumedicine/54462
- DOI
- 10.3390/catal11091134
- ISSN
- 2073-4344
2073-4344
- Abstract
- Catalysts based on (R, R)-1,2-diphenylethylenediamine are, as chiral organic catalysts, applied to the asymmetric Michael addition to alpha, beta-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 GABA(B) agonists in an optically pure manner. Additionally, GABA (gamma-aminobutyric acid) analogs such as baclofen and phenibut were synthesized as R-type S-type with high optical purity.
- Files in This Item
- There are no files associated with this item.
- Appears in
Collections - 1. Basic Science > Department of Anatomy > 1. Journal Articles
- 4. Research institute > Institute of Human Genetics > 1. Journal Articles
- 4. Research institute > Practical Anatomy Research Institute > 1. Journal Articles
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.