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

doi:10.3390/catal11091134

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

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

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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 GABA_B 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 language	English
Article number	1134
Journal	Catalysts
Volume	11
Issue number	9
DOIs	https://doi.org/10.3390/catal11091134
Publication status	Published - 2021 Sept

Keywords

Calcium release
Inhibitor of GABA receptor
Michael addition
Organic chemistry

ASJC Scopus subject areas

Catalysis
Environmental Science(all)
Physical and Theoretical Chemistry

Access to Document

10.3390/catal11091134

Cite this

@article{9b763146149440049406994bab4b2af7,

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

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.",

keywords = "Calcium release, Inhibitor of GABA receptor, Michael addition, Organic chemistry",

author = "Shim, {Jae Ho} and Yeonsun Hong and Kim, {Ji Hae} and Kim, {Hyeon Soo} and Ha, {Deok Chan}",

note = "Funding Information: Funding: This study was supported by the National Research Foundation of Korea (NRF-2021M3A9-G1097744), (NRF-2021R1A6A3A01087948). Also, this study was supported by a Korea University Grant. Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2021",

month = sep,

doi = "10.3390/catal11091134",

language = "English",

volume = "11",

journal = "Catalysts",

issn = "2073-4344",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "9",

}

TY - JOUR

T1 - Organocatalytic asymmetric michael addition in aqueous media by a hydrogen-bonding catalyst and application for inhibitors of gabab receptor

AU - Shim, Jae Ho

AU - Hong, Yeonsun

AU - Kim, Ji Hae

AU - Kim, Hyeon Soo

AU - Ha, Deok Chan

N1 - Funding Information: Funding: This study was supported by the National Research Foundation of Korea (NRF-2021M3A9-G1097744), (NRF-2021R1A6A3A01087948). Also, this study was supported by a Korea University Grant. Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2021/9

Y1 - 2021/9

N2 - 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.

AB - 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.

KW - Calcium release

KW - Inhibitor of GABA receptor

KW - Michael addition

KW - Organic chemistry

UR - http://www.scopus.com/inward/record.url?scp=85115134366&partnerID=8YFLogxK

U2 - 10.3390/catal11091134

DO - 10.3390/catal11091134

M3 - Article

AN - SCOPUS:85115134366

SN - 2073-4344

VL - 11

JO - Catalysts

JF - Catalysts

IS - 9

M1 - 1134

ER -