Title:
METHOD FOR SYNTHESIZING BETA-SUBSTITUTED GAMMA-NITRO DITHIOESTER COMPOUND, BETA-SUBSTITUTED GAMMA-NITRO DITHIOESTER COMPOUND PREPARED THEREBY, NOVEL GAMMA-AMINO ACID DERIVATIVE COMPOUND INDUCED THEREBY, AND METHOD FOR PREPARING BETA-SUBSTITUTED GAMMA-AMINOBUTYRIC ACID DERIVATIVE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2018/128386
Kind Code:
A1
Abstract:
Disclosed is a method for synthesizing a gamma-nitro dithioester derivative compound (a γ-nitro dithioester compound). The gamma-nitro dithioester derivative compound may be synthesized by subjecting a nitroalkene compound having two carbon-containing substituents at the beta position (a β,β-disubstituted nitroalkene compound) and a dithiomalonate compound to the Michael reaction in water or an aqueous inorganic salt solution under the presence of a catalyst comprising a base, and the gamma-nitro dithioester derivative compound synthesized thereby has two carbon-containing substituents at the beta position.
Inventors:
SONG CHOONG EUI (KR)
SIM JAE HUN (KR)
SIM JAE HUN (KR)
Application Number:
PCT/KR2018/000120
Publication Date:
July 12, 2018
Filing Date:
January 03, 2018
Export Citation:
Assignee:
RESEARCH & BUSINESS FOUND SUNGKYUNKWAN UNIV (KR)
International Classes:
C07C327/22; B01J31/02
Foreign References:
| KR101548885B1 | 2015-09-01 |
Other References:
JIN, H.: "L-Proline Derived Bifunctional Organocatalysts: Enantioselective Michael Addition of Dithiomalonates to trans-beta- Nitroolefins", JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 8, 18 March 2016 (2016-03-18), pages 3263 - 3274, XP055607140
SHI, X.: "Asymmetric Vinylogous Michael Addition/Cyclization Cascade Reaction for the Construction of Diversely Structured Spiro-Oxindole Skeletons", ADVANCED SYNTHESIS & CATALYSIS, vol. 355, no. 16, 2013, pages 3119 - 3123, XP055607143
REZNIKOV, A. N.: "Enantioselective synthesis of gamma-aminobutyric acid derivatives by Ni(II)-catalyzed reaction of diethyl malonate with nitroalkenes", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, vol. 49, no. 5, 2013, pages 663 - 668, XP055177126, DOI: doi:10.1134/S1070428013050047
DATABASE Chemical Abstract 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 89775-82-6
MA, C.: "Highly Enantioselective Michael Addition of Malonates to beta-CF3 -beta-(3-Indolyl)-nitroalkenes: Construction of Trifluoromethylated All-Carbon QuaternaryStereogenic Centres", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2014, no. 19, 23 May 2014 (2014-05-23), pages 3981 - 3985, XP055607146
KWIATKOWSKI, P.: "Efficient and Highly Enantioselective Construction of Trifluoromethylated Quaternary Stereogenic Centers via High-Pressure Mediated Organocatalytic Conjugate Addition of Nitromethane to beta,beta- Disubstituted Enones", ORGANIC LETTERS, vol. 16, no. 22, 2014, pages 5930 - 5933, XP055607149
DATABASE Chemical Abstract 1 December 2014 (2014-12-01), retrieved from STN Database accession no. 1637534-19-0
SIM, J. H.: "Water-Enabled Catalytic Asymmetric Michael Reactions of Unreactive Nitroalkenes: One-Pot Synthesis of Chiral GABA-Analogs with All-Carbon Quaternary Stereogenic Centers", ANGEWANDTE CHEMIE, vol. 129, no. 7, 18 January 2017 (2017-01-18), pages 1861 - 1865, XP055607151
SHI, X.: "Asymmetric Vinylogous Michael Addition/Cyclization Cascade Reaction for the Construction of Diversely Structured Spiro-Oxindole Skeletons", ADVANCED SYNTHESIS & CATALYSIS, vol. 355, no. 16, 2013, pages 3119 - 3123, XP055607143
REZNIKOV, A. N.: "Enantioselective synthesis of gamma-aminobutyric acid derivatives by Ni(II)-catalyzed reaction of diethyl malonate with nitroalkenes", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, vol. 49, no. 5, 2013, pages 663 - 668, XP055177126, DOI: doi:10.1134/S1070428013050047
DATABASE Chemical Abstract 16 November 1984 (1984-11-16), retrieved from STN Database accession no. 89775-82-6
MA, C.: "Highly Enantioselective Michael Addition of Malonates to beta-CF3 -beta-(3-Indolyl)-nitroalkenes: Construction of Trifluoromethylated All-Carbon QuaternaryStereogenic Centres", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2014, no. 19, 23 May 2014 (2014-05-23), pages 3981 - 3985, XP055607146
KWIATKOWSKI, P.: "Efficient and Highly Enantioselective Construction of Trifluoromethylated Quaternary Stereogenic Centers via High-Pressure Mediated Organocatalytic Conjugate Addition of Nitromethane to beta,beta- Disubstituted Enones", ORGANIC LETTERS, vol. 16, no. 22, 2014, pages 5930 - 5933, XP055607149
DATABASE Chemical Abstract 1 December 2014 (2014-12-01), retrieved from STN Database accession no. 1637534-19-0
SIM, J. H.: "Water-Enabled Catalytic Asymmetric Michael Reactions of Unreactive Nitroalkenes: One-Pot Synthesis of Chiral GABA-Analogs with All-Carbon Quaternary Stereogenic Centers", ANGEWANDTE CHEMIE, vol. 129, no. 7, 18 January 2017 (2017-01-18), pages 1861 - 1865, XP055607151
Attorney, Agent or Firm:
NAM, Gun Pil et al. (KR)
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