Title:
METHOD FOR STEREOSPECIFIC SYNTHESIS OF 2-ENAL AND 2-ENONE COMPOUNDS, AND DEUTERATED COMPOUNDS THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/127712
Kind Code:
A1
Abstract:
Disclosed is a method for stereospecific synthesis of 2-enal and 2-enone compounds, and deuterated compounds thereof, comprising reacting 2,3-dienol with organic boric acid, in an organic solvent under the action of a rhodium catalyst, a copper catalyst, a base, and air (or oxygen) to perform stereospecific one-step synthesis of 2-enal and 2-enone compounds, and deuterated compounds thereof. The method of the present invention involves simple operations, easily available raw materials and reagents, mild reaction conditions, widely applicable base material, good functional group compatibility, and stereospecific (single configuration) reaction. The method of the present invention can be used for the synthesis of deuterated 2-enal and deuterated 2-enone, and the structural modification of drug molecules and natural product molecules.
Inventors:
MA SHENGMING (CN)
WANG WEIYI (CN)
YU YIBO (CN)
QIAN HUI (CN)
WANG WEIYI (CN)
YU YIBO (CN)
QIAN HUI (CN)
Application Number:
PCT/CN2021/137207
Publication Date:
June 23, 2022
Filing Date:
December 10, 2021
Export Citation:
Assignee:
UNIV FUDAN (CN)
International Classes:
C07C45/00; C07C47/00; C07C49/00
Foreign References:
| CN102153472A | 2011-08-17 | |||
| CN1724499A | 2006-01-25 |
Other References:
CHOI SOO YOUNG, CHUNG YOUNG KEUN: "N-Heterocyclic Carbene (NHC)-Rhodium-Catalyzed Carbonylative CC Bond Formation of Allenols with Arylboronic Acids under Carbon Monoxide", ADVANCED SYNTHESIS AND CATALYSIS, vol. 353, no. 14-15, 1 October 2011 (2011-10-01), pages 2609 - 2613, XP055942682, ISSN: 1615-4150, DOI: 10.1002/adsc.201100309
DENG, YOU-QIAN ·, GU, ZHEN-HUA MA, SHENG-MING: "Reactions of 2,3-Allenols and Their Derivatives", CHINESE JOURNAL OF ORGANIC CHEMISTRY, vol. 26, no. 11, 30 November 2006 (2006-11-30), pages 1468 - 1484, XP055942690
DENG, YOU-QIAN ·, GU, ZHEN-HUA MA, SHENG-MING: "Reactions of 2,3-Allenols and Their Derivatives", CHINESE JOURNAL OF ORGANIC CHEMISTRY, vol. 26, no. 11, 30 November 2006 (2006-11-30), pages 1468 - 1484, XP055942690
MA SHENGMING, JIAO NING, YE LONGWU: "Palladium-Catalyzed Highly Regio- and Stereoselective Addition of Organoboronic Acids to Allenes in the Presence of AcOH", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 9, no. 24, 15 December 2003 (2003-12-15), DE, pages 6049 - 6056, XP055942684, ISSN: 0947-6539, DOI: 10.1002/chem.200305301
ZHAO YUYANG, WANG YURONG, GU ZHANSHOU, WANG ZHIMING: "[3,3]-Sigmatropic rearrangement of allenic alcohols: stereoselective synthesis of 1,3-diene-2-ol sulfonates", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 15, no. 18, 1 January 2017 (2017-01-01), pages 4014 - 4021, XP055942686, ISSN: 1477-0520, DOI: 10.1039/C7OB00578D
DENG, YOU-QIAN ·, GU, ZHEN-HUA MA, SHENG-MING: "Reactions of 2,3-Allenols and Their Derivatives", CHINESE JOURNAL OF ORGANIC CHEMISTRY, vol. 26, no. 11, 30 November 2006 (2006-11-30), pages 1468 - 1484, XP055942690
DENG, YOU-QIAN ·, GU, ZHEN-HUA MA, SHENG-MING: "Reactions of 2,3-Allenols and Their Derivatives", CHINESE JOURNAL OF ORGANIC CHEMISTRY, vol. 26, no. 11, 30 November 2006 (2006-11-30), pages 1468 - 1484, XP055942690
MA SHENGMING, JIAO NING, YE LONGWU: "Palladium-Catalyzed Highly Regio- and Stereoselective Addition of Organoboronic Acids to Allenes in the Presence of AcOH", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 9, no. 24, 15 December 2003 (2003-12-15), DE, pages 6049 - 6056, XP055942684, ISSN: 0947-6539, DOI: 10.1002/chem.200305301
ZHAO YUYANG, WANG YURONG, GU ZHANSHOU, WANG ZHIMING: "[3,3]-Sigmatropic rearrangement of allenic alcohols: stereoselective synthesis of 1,3-diene-2-ol sulfonates", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 15, no. 18, 1 January 2017 (2017-01-01), pages 4014 - 4021, XP055942686, ISSN: 1477-0520, DOI: 10.1039/C7OB00578D
Attorney, Agent or Firm:
MSJLAW OFFICE (CN)
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