Title:
METHOD FOR PRODUCING ASYMMETRIC RING-OPENING REACTION PRODUCT OF CYCLIC ANHYDRIDE USING ORGANIC CHIRAL CATALYST COMPOUNDS
Document Type and Number:
WIPO Patent Application WO/2024/034746
Kind Code:
A1
Abstract:
The present invention relates to a method for producing a chiral carbonyl derivative using an (R,R)-1,2-diphenylethylenediamine (DPEN)-based thiourea catalyst compound. According to the production method, a chiral carbonyl derivative having high enantioselectivity can be prepared in excellent yield through an asymmetric ring-opening reaction between a cyclic anhydride and a thiol (-SH) or an amine (NH2), that is, a sulfur decomposition reaction (thiolysis) or a nitrogen decomposition reaction (aminolysis).
Inventors:
SHIM JAE HO (KR)
KIM HYEON SOO (KR)
KIM HYEON SOO (KR)
Application Number:
PCT/KR2022/018735
Publication Date:
February 15, 2024
Filing Date:
November 24, 2022
Export Citation:
Assignee:
UNIV KOREA RES & BUS FOUND (KR)
International Classes:
C07C327/24; B01J31/02; C07C231/10; C07C235/72; C07C235/82; C07C327/22; C07D207/40
Foreign References:
| US20090253919A1 | 2009-10-08 |
Other References:
SCHMITT, E. ; SCHIFFERS, I. ; BOLM, C.: "Highly enantioselective desymmetrizations of meso-anhydrides", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 66, no. 33, 14 August 2010 (2010-08-14), AMSTERDAM, NL , pages 6349 - 6357, XP027154224, ISSN: 0040-4020
JANG HYEONG BIN, RHO HO SIK, OH JOONG SUK, NAM EUN HYE, PARK SANG EUN, BAE HAN YONG, SONG CHOONG EUI: "DOSY NMR for monitoring self aggregation of bifunctional organocatalysts: increasing enantioselectivity with decreasing catalyst concentration", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 8, no. 17, 1 January 2010 (2010-01-01), pages 3918, XP093138931, ISSN: 1477-0520, DOI: 10.1039/c0ob00047g
HONG‐JUN YANG; FANG‐JUN XIONG; XIAO‐FEI CHEN; FEN‐ER CHEN: "Highly Enantioselective Thiolysis of Prochiral Cyclic Anhydrides Catalyzed by Amino Alcohol Bifunctional Organocatalysts and Its Application to the Synthesis of Pregabalin", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2013, no. 21, 17 June 2013 (2013-06-17), DE , pages 4495 - 4498, XP072106733, ISSN: 1434-193X, DOI: 10.1002/ejoc.201300464
BASTIDA DAVID, LIU YANKAI, TIAN XU, ESCUDERO-ADÁN EDUARDO, MELCHIORRE PAOLO: "Asymmetric Vinylogous Aldol Reaction via H-Bond-Directing Dienamine Catalysis", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 15, no. 1, 4 January 2013 (2013-01-04), US , pages 220 - 223, XP093138936, ISSN: 1523-7060, DOI: 10.1021/ol303312p
R. KNORR ET AL.: "New coupling reagents in peptide chemistry", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 30, no. 15, 1 January 1989 (1989-01-01), Amsterdam , NL , pages 1927 - 1930, XP002294410, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)99616-3
BENJAMIN ELLIS, HIJJI YOUSEF: "The Synthesis of Unsubstituted Cyclic Imides Using Hydroxylamine under Microwave Irradiation", MOLECULES, MDPI AG, CH, vol. 13, no. 1, 25 January 2008 (2008-01-25), CH , pages 157 - 169, XP093138940, ISSN: 1420-3049, DOI: 10.3390/molecules13010157
SHIM JAE HO, PARK SUNG JOO, AHN BYUNG KOOK, LEE JI YEON, KIM HYEON SOO, HA DEOK-CHAN: "Enantioselective Thiolysis and Aminolysis of Cyclic Anhydrides Using a Chiral Diamine-Derived Thiourea Catalyst", ACS OMEGA, ACS PUBLICATIONS, US, vol. 6, no. 50, 21 December 2021 (2021-12-21), US , pages 34501 - 34511, XP093138943, ISSN: 2470-1343, DOI: 10.1021/acsomega.1c04741
JANG HYEONG BIN, RHO HO SIK, OH JOONG SUK, NAM EUN HYE, PARK SANG EUN, BAE HAN YONG, SONG CHOONG EUI: "DOSY NMR for monitoring self aggregation of bifunctional organocatalysts: increasing enantioselectivity with decreasing catalyst concentration", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 8, no. 17, 1 January 2010 (2010-01-01), pages 3918, XP093138931, ISSN: 1477-0520, DOI: 10.1039/c0ob00047g
HONG‐JUN YANG; FANG‐JUN XIONG; XIAO‐FEI CHEN; FEN‐ER CHEN: "Highly Enantioselective Thiolysis of Prochiral Cyclic Anhydrides Catalyzed by Amino Alcohol Bifunctional Organocatalysts and Its Application to the Synthesis of Pregabalin", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2013, no. 21, 17 June 2013 (2013-06-17), DE , pages 4495 - 4498, XP072106733, ISSN: 1434-193X, DOI: 10.1002/ejoc.201300464
BASTIDA DAVID, LIU YANKAI, TIAN XU, ESCUDERO-ADÁN EDUARDO, MELCHIORRE PAOLO: "Asymmetric Vinylogous Aldol Reaction via H-Bond-Directing Dienamine Catalysis", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 15, no. 1, 4 January 2013 (2013-01-04), US , pages 220 - 223, XP093138936, ISSN: 1523-7060, DOI: 10.1021/ol303312p
R. KNORR ET AL.: "New coupling reagents in peptide chemistry", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 30, no. 15, 1 January 1989 (1989-01-01), Amsterdam , NL , pages 1927 - 1930, XP002294410, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)99616-3
BENJAMIN ELLIS, HIJJI YOUSEF: "The Synthesis of Unsubstituted Cyclic Imides Using Hydroxylamine under Microwave Irradiation", MOLECULES, MDPI AG, CH, vol. 13, no. 1, 25 January 2008 (2008-01-25), CH , pages 157 - 169, XP093138940, ISSN: 1420-3049, DOI: 10.3390/molecules13010157
SHIM JAE HO, PARK SUNG JOO, AHN BYUNG KOOK, LEE JI YEON, KIM HYEON SOO, HA DEOK-CHAN: "Enantioselective Thiolysis and Aminolysis of Cyclic Anhydrides Using a Chiral Diamine-Derived Thiourea Catalyst", ACS OMEGA, ACS PUBLICATIONS, US, vol. 6, no. 50, 21 December 2021 (2021-12-21), US , pages 34501 - 34511, XP093138943, ISSN: 2470-1343, DOI: 10.1021/acsomega.1c04741
Attorney, Agent or Firm:
MUHANN PATENT & LAW FIRM (KR)
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