Title:
METHOD FOR MANUFACTURING OPTICALLY ACTIVE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2015/141564
Kind Code:
A1
Abstract:
Provided is a method for manufacturing an optically active compound represented by formula (2), the method comprising bringing hydrogen and a compound represented by formula (1) into contact in the presence of a transition metal catalyst having an optically active ligand. In the formulae: R1 represents a hydrogen atom or an acetyl group; R2, R3, R4, and R5 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a nitro group, an amino group, or an acyl group; R6 represents an alkyl group; R7 and R8 each independently represent a hydrogen atom or an alkyl group; and the carbon atom indicated by an asterisk (*) is an asymmetric carbon atom.
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Inventors:
TAKAHASHI TOMOAKI (JP)
UJITA SATORU (JP)
UJITA SATORU (JP)
Application Number:
PCT/JP2015/057395
Publication Date:
September 24, 2015
Filing Date:
March 06, 2015
Export Citation:
Assignee:
SUMITOMO CHEMICAL CO (JP)
International Classes:
C07D215/04; C07D215/08; C07B53/00; C07B61/00
Foreign References:
| US4087561A | 1978-05-02 | |||
| JP2002187895A | 2002-07-05 |
Other References:
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OKA,H. ET AL.: "Synthesis and characterization of poly(1,3-phenylene)-based polyradicals carrying cyclic aminoxyls", JOURNAL OF MATERIALS CHEMISTRY, vol. 11, no. 5, 2001, pages 1364 - 1369, XP008104614
RYBAKOV,V.B. ET AL.: "6-Ethoxy-1,2,3,4-tetrahydro -2,2,4-trimethylquinoline, Acta Crystallographica", SECTION E: STRUCTURE REPORTS, vol. 60, no. 7, 2004, pages o1145 - o1146
CSJ: THE CHEMICAL SOCIETY OF JAPAN, KOGAKU ISEITAI NO BUNRI [KIKAN KAGAKU SOSETSU NO.6, 10 October 1989 (1989-10-10), pages 16 - 29 , 212 to 225
TETSUO NAGANO ET AL., TOKYO KAGAKU DOJIN, 27 February 2004 (2004-02-27), pages 163 - 168
WERMUTH, C.G., SAISHIN SOYAKU KAGAKU JOKAN, 15 August 1998 (1998-08-15), pages 475 - 501
TANG,W. ET AL.: "New Chiral Phosphorus Ligands for Enantioselective Hydrogenation", CHEMICAL REVIEWS, vol. 103, no. 8, 2003, pages 3029 - 3069, XP002284690
SMIDT,S.P. ET AL.: "SimplePHOX, a Readily Available Chiral Ligand System for Iridium- Catalyzed Asymmetric Hydrogenation", ORGANIC LETTERS, vol. 6, no. 12, 2004, pages 2023 - 2026, XP055225290
BAEZA,A. ET AL.: "Iridium-Catalyzed Asymmetric Hydrogenation of N-Protected Indoles", CHEMISTRY - A EUROPEAN JOURNAL, vol. 16, no. 7, 2010, pages 2036 - 2039 , S2036/1-S2036/25, XP055225292
CHURCH,T.L. ET AL.: "Enantioselectivity in the Iridium-Catalyzed Hydrogenation of Unfunctionalized Olefins", ORGANOMETALLICS, vol. 29, no. 24, 2010, pages 6769 - 6781, XP055225293
NANCHEN,S. ET AL.: "Synthesis and application of chiral N-heterocyclic carbene-oxazoline ligands: iridium-catalyzed enantioselective hydrogenation", CHEMISTRY - A EUROPEAN JOURNAL, vol. 12, no. 17, 2006, pages 4550 - 4558, XP055184826
GOULIOUKINA,N.S. ET AL.: "Highly enantioselective hydrogenation of alpha,beta-unsaturated phosphonates with iridium-phosphinooxazoline complex: Synthesis of a phosphorus analogue of naproxen", TETRAHEDRON : ASYMMETRY, vol. 14, no. 10, 2003, pages 1397 - 1401, XP004439177
OKA,H. ET AL.: "Synthesis and characterization of poly(1,3-phenylene)-based polyradicals carrying cyclic aminoxyls", JOURNAL OF MATERIALS CHEMISTRY, vol. 11, no. 5, 2001, pages 1364 - 1369, XP008104614
RYBAKOV,V.B. ET AL.: "6-Ethoxy-1,2,3,4-tetrahydro -2,2,4-trimethylquinoline, Acta Crystallographica", SECTION E: STRUCTURE REPORTS, vol. 60, no. 7, 2004, pages o1145 - o1146
CSJ: THE CHEMICAL SOCIETY OF JAPAN, KOGAKU ISEITAI NO BUNRI [KIKAN KAGAKU SOSETSU NO.6, 10 October 1989 (1989-10-10), pages 16 - 29 , 212 to 225
TETSUO NAGANO ET AL., TOKYO KAGAKU DOJIN, 27 February 2004 (2004-02-27), pages 163 - 168
WERMUTH, C.G., SAISHIN SOYAKU KAGAKU JOKAN, 15 August 1998 (1998-08-15), pages 475 - 501
TANG,W. ET AL.: "New Chiral Phosphorus Ligands for Enantioselective Hydrogenation", CHEMICAL REVIEWS, vol. 103, no. 8, 2003, pages 3029 - 3069, XP002284690
SMIDT,S.P. ET AL.: "SimplePHOX, a Readily Available Chiral Ligand System for Iridium- Catalyzed Asymmetric Hydrogenation", ORGANIC LETTERS, vol. 6, no. 12, 2004, pages 2023 - 2026, XP055225290
BAEZA,A. ET AL.: "Iridium-Catalyzed Asymmetric Hydrogenation of N-Protected Indoles", CHEMISTRY - A EUROPEAN JOURNAL, vol. 16, no. 7, 2010, pages 2036 - 2039 , S2036/1-S2036/25, XP055225292
CHURCH,T.L. ET AL.: "Enantioselectivity in the Iridium-Catalyzed Hydrogenation of Unfunctionalized Olefins", ORGANOMETALLICS, vol. 29, no. 24, 2010, pages 6769 - 6781, XP055225293
NANCHEN,S. ET AL.: "Synthesis and application of chiral N-heterocyclic carbene-oxazoline ligands: iridium-catalyzed enantioselective hydrogenation", CHEMISTRY - A EUROPEAN JOURNAL, vol. 12, no. 17, 2006, pages 4550 - 4558, XP055184826
GOULIOUKINA,N.S. ET AL.: "Highly enantioselective hydrogenation of alpha,beta-unsaturated phosphonates with iridium-phosphinooxazoline complex: Synthesis of a phosphorus analogue of naproxen", TETRAHEDRON : ASYMMETRY, vol. 14, no. 10, 2003, pages 1397 - 1401, XP004439177
Attorney, Agent or Firm:
NAKAYAMA, Tohru et al. (JP)
Nakayama δΊ¨ (JP)
Nakayama δΊ¨ (JP)
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