Title:
METHOD FOR DIRECTLY CONSTRUCTING TETRA-SUBSTITUTED ALLENIC ACID COMPOUND HAVING HIGH OPTICAL ACTIVITY
Document Type and Number:
WIPO Patent Application WO/2020/119549
Kind Code:
A1
Abstract:
Disclosed is a method for directly constructing a tetra-substituted allenic acid compound having high optical activity. An optically active allenic acid compound is directly constructed in one step by reacting tertiary propargyl alcohol, carbon monoxide and water with axial chirality in an organic solvent under the action of a palladium catalyst, a chiral bisphosphine ligand, a monophosphine ligand, and an organic phosphoric acid. The optically active allenic acid compound can be used as an intermediate to construct γ-butyrolactone compounds containing a tetra-substituted chiral quaternary carbon core, and tetra-substituted allenol compounds.
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Inventors:
MA SHENGMING (CN)
ZHENG WEIFENG (CN)
QIAN HUI (CN)
ZHENG WEIFENG (CN)
QIAN HUI (CN)
Application Number:
PCT/CN2019/123005
Publication Date:
June 18, 2020
Filing Date:
December 04, 2019
Export Citation:
Assignee:
UNIV FUDAN (CN)
International Classes:
C07C51/12; C07C51/14; C07C57/00; C07C57/03
Foreign References:
| CN108976123A | 2018-12-11 | |||
| CN107176899A | 2017-09-19 | |||
| CN1293190A | 2001-05-02 |
Other References:
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TAKUYA HASHIMOTO ET AL: "Phase-transfer-catalysed Asymmetric Synthesis of Tetrasubstituted Allenes", NATURE CHEMISTRY, vol. 5, no. 3, 10 February 2013 (2013-02-10), pages 240 - 244, XP055712059, ISSN: 1755-4349, DOI: 10.1038/nchem.1567
SOWMIANARAYANAN RAMASWAMY ET AL: "Enantiomerically Selective Pig Liver Esterase-catalysed Hydrolyses of Racemic Allenic Esters", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 20, 31 December 1986 (1986-12-31), pages 1545 - 1546, XP055712060, ISSN: 0022-4936, DOI: 10.1039/c39860001545
ERNST RUCH ET AL: "Experimentelle Prüfung von Näherungsansätzen für Chiralitätsfunktionen am Beispiel der optischen Aktivität von Allen-Derivaten im Transparenzgebiet", ANGEW. CHEM, vol. 85, no. 1, 1 January 1973 (1973-01-01), pages 10 - 15, XP055712070, ISSN: 1521-3757
WEIFENG ZHENG ET AL: "2, 3-Allenoic Acids via Palladium-catalyzed Carboxylation of Propargylic Alcohols", ORGANIC CHEMISTRY FRONTIERS, vol. 5, no. 12, 25 April 2018 (2018-04-25), pages 1900 - 1904, XP055712074, ISSN: 2052-4129, DOI: 10.1039/C8QO00318A
HOFFMANN-RODER, AKRAUSE, N, ANGEW. CHEM., vol. 43, 2004, pages 1196
RIVERA-FUENTES, PDIEDERICH, F, ANGEW. CHEM., vol. 51, 2012, pages 2818
HAYASHI, TTOKUNAGA, NINOUE, K, ORG. LETT., vol. 6, 2004, pages 305
QIAN, DWU, LLIN, ZSUN, J, NAT. COMMUN., vol. 8, 2017, pages 567
HASHIMOTO, TSAKATA, KTAMAKUNI, FDUTTON, M. J.MARUOKA, K, NAT. CHEM., vol. 5, 2013, pages 240
MBOFANA, C. T.MILLER, S. J., J. AM. CHEM. SOC., vol. 136, 2014, pages 3285
WANG, GLIU, XCHEN, YYANG, JLI, J; LIN, LFENG, X, ACS CATAL, vol. 6, 2016, pages 2482
TANG, YXU, JYANG, JLIN, LFENG, XLIU, X, CHEM, vol. 4, 2018, pages 1658
TAP, ABLOND, AWAKCHAURE, V. N.LIST, B, ANGEW. CHEM., vol. 55, 2016, pages 8962
MA, SWU, S, CHEM. COMMUN., vol. 0, 2001, pages 441
AO, Y-FWANG, D.-X.ZHAO, LWANG, M.-X., J. ORG. CHEM., vol. 79, 2014, pages 3103
MARSHALL, J. A.BARTLEY, G. S.WALLACE, E. M., J. ORG. CHEM., vol. 61, 1996, pages 5729
YU, JCHEN, W.-J.GONG, L.-Z., ORG. LETT., vol. 12, 2010, pages 4050
See also references of EP 3896053A4
TAKUYA HASHIMOTO ET AL: "Phase-transfer-catalysed Asymmetric Synthesis of Tetrasubstituted Allenes", NATURE CHEMISTRY, vol. 5, no. 3, 10 February 2013 (2013-02-10), pages 240 - 244, XP055712059, ISSN: 1755-4349, DOI: 10.1038/nchem.1567
SOWMIANARAYANAN RAMASWAMY ET AL: "Enantiomerically Selective Pig Liver Esterase-catalysed Hydrolyses of Racemic Allenic Esters", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 20, 31 December 1986 (1986-12-31), pages 1545 - 1546, XP055712060, ISSN: 0022-4936, DOI: 10.1039/c39860001545
ERNST RUCH ET AL: "Experimentelle Prüfung von Näherungsansätzen für Chiralitätsfunktionen am Beispiel der optischen Aktivität von Allen-Derivaten im Transparenzgebiet", ANGEW. CHEM, vol. 85, no. 1, 1 January 1973 (1973-01-01), pages 10 - 15, XP055712070, ISSN: 1521-3757
WEIFENG ZHENG ET AL: "2, 3-Allenoic Acids via Palladium-catalyzed Carboxylation of Propargylic Alcohols", ORGANIC CHEMISTRY FRONTIERS, vol. 5, no. 12, 25 April 2018 (2018-04-25), pages 1900 - 1904, XP055712074, ISSN: 2052-4129, DOI: 10.1039/C8QO00318A
HOFFMANN-RODER, AKRAUSE, N, ANGEW. CHEM., vol. 43, 2004, pages 1196
RIVERA-FUENTES, PDIEDERICH, F, ANGEW. CHEM., vol. 51, 2012, pages 2818
HAYASHI, TTOKUNAGA, NINOUE, K, ORG. LETT., vol. 6, 2004, pages 305
QIAN, DWU, LLIN, ZSUN, J, NAT. COMMUN., vol. 8, 2017, pages 567
HASHIMOTO, TSAKATA, KTAMAKUNI, FDUTTON, M. J.MARUOKA, K, NAT. CHEM., vol. 5, 2013, pages 240
MBOFANA, C. T.MILLER, S. J., J. AM. CHEM. SOC., vol. 136, 2014, pages 3285
WANG, GLIU, XCHEN, YYANG, JLI, J; LIN, LFENG, X, ACS CATAL, vol. 6, 2016, pages 2482
TANG, YXU, JYANG, JLIN, LFENG, XLIU, X, CHEM, vol. 4, 2018, pages 1658
TAP, ABLOND, AWAKCHAURE, V. N.LIST, B, ANGEW. CHEM., vol. 55, 2016, pages 8962
MA, SWU, S, CHEM. COMMUN., vol. 0, 2001, pages 441
AO, Y-FWANG, D.-X.ZHAO, LWANG, M.-X., J. ORG. CHEM., vol. 79, 2014, pages 3103
MARSHALL, J. A.BARTLEY, G. S.WALLACE, E. M., J. ORG. CHEM., vol. 61, 1996, pages 5729
YU, JCHEN, W.-J.GONG, L.-Z., ORG. LETT., vol. 12, 2010, pages 4050
See also references of EP 3896053A4
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MSJLAW OFFICE (CN)
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