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Title:
BIFUNCTIONAL CHIRAL ORGANOCATALYTIC COMPOUND HAVING EXCELLENT ENANTIOSELECTIVITY, PREPARATION METHOD THEREFOR, AND METHOD FOR PRODUCING NON-NATURAL GAMMA-AMINO ACID FROM NITRO COMPOUND BY USING SAME
Document Type and Number:
WIPO Patent Application WO/2019/168269
Kind Code:
A1
Abstract:
The present invention relates to a bifunctional chiral organocatalytic compound having excellent enantioselectivity, a preparation method therefor, and a method for producing a non-natural gamma amino acid from a nitro compound by using the chiral organocatalytic compound. According to the present invention, the bifunctional chiral organocatalytic compound having excellent enantioselectivity can be easily synthesized, gamma-amino acids with high optical selectivity can be obtained at a high yield by an economical and convenient method using the chiral organocatalytic compound, and various (R)-configuration gamma-amino acids, which are not present in nature, can be produced with high optical purity in large quantities by using a small amount of a catalyst, and therefore, the present invention can be widely utilized in various industrial fields including the pharmaceutical industry.

Inventors:
HA DEOK-CHAN (KR)
SHIM JAE HO (KR)
Application Number:
PCT/KR2019/001003
Publication Date:
September 06, 2019
Filing Date:
January 24, 2019
Export Citation:
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Assignee:
UNIV KOREA RES & BUS FOUND (KR)
International Classes:
B01J31/02; B01J37/00; C07C201/12; C07C205/04; C07C227/22; C07C229/36
Foreign References:
JP2007332129A2007-12-27
Other References:
LU , A: "Enantioselective Synthesis of trans-Dihydrobenzofurans via Primary Amine-Thiourea Organocatalyzed Intramolecular Michael Addition", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 14, 21 June 2012 (2012-06-21), pages 6208 - 6214, XP055634732, ISSN: 0022-3263, DOI: 10.1021/jo301006e
ZHANG, J.: "Michael-Michael Addition Reactions Promoted by Secondary Amine-Thiourea: Stereocontrolled Construction of Barbiturate-Fused Tetrahydropyrano Scaffolds and Pyranocoumarins", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 24, 2017, pages 13594 - 13601, XP055634737, ISSN: 0022-3263, DOI: 10.1021/acs.joc.7b01902
MENINNO, S.: "Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter", BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 12, 2016, pages 643 - 647, XP055634740, DOI: 10.3762/bjoc.12.63
HAN, B.: "Discovery of Bifunctional Thiourea/Secondary-Amine Organocatalysts for the Highly Stereoselective Nitro-Mannich Reaction of a-Substituted Nitroacetates", CHEMISTRY-A EUROPEAN JOURNAL, vol. 14, no. 27, 2008, pages 8094 - 8097, XP055634746
ORGANOCATALYTIC ASYMMETRIC MICHAEL ADDITIONS OF KETONES TO ALPHA,BETA-UNSATURATED NITRO COMPOUNDS, vol. 1 - 117, February 2017 (2017-02-01), pages 7 - 19
Attorney, Agent or Firm:
JUNG, Eun Youl (KR)
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