Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABA<sub>B</sub> Receptor
Catalysts based on (<i>R</i>, <i>R</i>)-1,2-diphenylethylenediamine are, as chiral organic catalysts, applied to the asymmetric Michael addition to <i>α</i>, <i>β</i>-unsaturated nitroalkenes under neutral conditions. The role of an aqueous medium for...
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MDPI AG
2021-09-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/11/9/1134 |
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| author | Jae Ho Shim Yeonsun Hong Ji Hae Kim Hyeon Soo Kim Deok-Chan Ha |
| author_facet | Jae Ho Shim Yeonsun Hong Ji Hae Kim Hyeon Soo Kim Deok-Chan Ha |
| author_sort | Jae Ho Shim |
| collection | DOAJ |
| description | Catalysts based on (<i>R</i>, <i>R</i>)-1,2-diphenylethylenediamine are, as chiral organic catalysts, applied to the asymmetric Michael addition to <i>α</i>, <i>β</i>-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-(CF<sub>3</sub>)<sub>2</sub>-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<sub>B</sub> agonists in an optically pure manner. Additionally, GABA (<i>γ</i>-aminobutyric acid) analogs such as baclofen and phenibut were synthesized as <i>R</i>-type <i>S</i>-type with high optical purity. |
| first_indexed | 2024-03-10T07:49:12Z |
| format | Article |
| id | doaj.art-4afc761ebc1a4e1a94bdb10519125405 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T07:49:12Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-4afc761ebc1a4e1a94bdb105191254052023-11-22T12:21:57ZengMDPI AGCatalysts2073-43442021-09-01119113410.3390/catal11091134Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABA<sub>B</sub> ReceptorJae Ho Shim0Yeonsun Hong1Ji Hae Kim2Hyeon Soo Kim3Deok-Chan Ha4Department of Anatomy, Korea University College of Medicine, 126-1, Anam-dong 5-ga, Seoul 02841, KoreaDavid H. Smith Center for Vaccine Biology and Immunology, Department of Microbiology and Immunology, University of Rochester, Rochester, NY 14642, USADepartment of Anatomy, Korea University College of Medicine, 126-1, Anam-dong 5-ga, Seoul 02841, KoreaDepartment of Anatomy, Korea University College of Medicine, 126-1, Anam-dong 5-ga, Seoul 02841, KoreaDepartment of Chemistry, Korea University College of Science, Anam-ro, Seoul 136701, KoreaCatalysts based on (<i>R</i>, <i>R</i>)-1,2-diphenylethylenediamine are, as chiral organic catalysts, applied to the asymmetric Michael addition to <i>α</i>, <i>β</i>-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-(CF<sub>3</sub>)<sub>2</sub>-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<sub>B</sub> agonists in an optically pure manner. Additionally, GABA (<i>γ</i>-aminobutyric acid) analogs such as baclofen and phenibut were synthesized as <i>R</i>-type <i>S</i>-type with high optical purity.https://www.mdpi.com/2073-4344/11/9/1134Michael additioninhibitor of GABA<sub>B</sub> receptororganic chemistrycalcium release |
| spellingShingle | Jae Ho Shim Yeonsun Hong Ji Hae Kim Hyeon Soo Kim Deok-Chan Ha Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABA<sub>B</sub> Receptor Catalysts Michael addition inhibitor of GABA<sub>B</sub> receptor organic chemistry calcium release |
| title | Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABA<sub>B</sub> Receptor |
| title_full | Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABA<sub>B</sub> Receptor |
| title_fullStr | Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABA<sub>B</sub> Receptor |
| title_full_unstemmed | Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABA<sub>B</sub> Receptor |
| title_short | Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABA<sub>B</sub> Receptor |
| title_sort | organocatalytic asymmetric michael addition in aqueous media by a hydrogen bonding catalyst and application for inhibitors of gaba sub b sub receptor |
| topic | Michael addition inhibitor of GABA<sub>B</sub> receptor organic chemistry calcium release |
| url | https://www.mdpi.com/2073-4344/11/9/1134 |
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