WO2008140074A1 - Method for production of optically active carboxylic acid ester - Google Patents

Method for production of optically active carboxylic acid ester Download PDF

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Publication number
WO2008140074A1
WO2008140074A1 PCT/JP2008/058743 JP2008058743W WO2008140074A1 WO 2008140074 A1 WO2008140074 A1 WO 2008140074A1 JP 2008058743 W JP2008058743 W JP 2008058743W WO 2008140074 A1 WO2008140074 A1 WO 2008140074A1
Authority
WO
WIPO (PCT)
Prior art keywords
carboxylic acid
acid ester
optically active
active carboxylic
production
Prior art date
Application number
PCT/JP2008/058743
Other languages
French (fr)
Japanese (ja)
Inventor
Isamu Shiina
Kenya Nakata
Original Assignee
Tokyo University Of Science Educational Foundation Administrative Organization
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tokyo University Of Science Educational Foundation Administrative Organization filed Critical Tokyo University Of Science Educational Foundation Administrative Organization
Priority to JP2009514165A priority Critical patent/JP5417560B2/en
Publication of WO2008140074A1 publication Critical patent/WO2008140074A1/en

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215—Sulfur-containing compounds
    • B01J31/0218—Sulfides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0245—Nitrogen containing compounds being derivatives of carboxylic or carbonic acids
    • B01J31/0247—Imides, amides or imidates (R-C=NR(OR))
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyrane Compounds (AREA)

Abstract

Disclosed is a method for producing an optically active carboxylic acid ester directly from a racemic secondary alcohol and a carboxylic acid. Also disclosed is a method for optically resolving a racemic secondary alcohol in the same method as the above-mentioned method. One of the enantiomers of a racemic secondary alcohol and a carboxylic acid are subjected to the dehydrative condensation in the presence of benzoic anhydride or a derivative thereof by using (-)-tetramisole, (+)-tetramisole, (-)-benzotetramisole, (+)-benzotetramisole or the like as an asymmetric esterification catalyst, thereby producing an optically active carboxylic acid ester; and the other of the enantiomers, which is unreacted, is optically resolved.
PCT/JP2008/058743 2007-05-14 2008-05-12 Method for production of optically active carboxylic acid ester WO2008140074A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2009514165A JP5417560B2 (en) 2007-05-14 2008-05-12 Method for producing optically active carboxylic acid ester

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2007-128540 2007-05-14
JP2007128540 2007-05-14
JP2008061394 2008-03-11
JP2008-061394 2008-03-11

Publications (1)

Publication Number Publication Date
WO2008140074A1 true WO2008140074A1 (en) 2008-11-20

Family

ID=40002264

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/058743 WO2008140074A1 (en) 2007-05-14 2008-05-12 Method for production of optically active carboxylic acid ester

Country Status (2)

Country Link
JP (1) JP5417560B2 (en)
WO (1) WO2008140074A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009113428A1 (en) * 2008-03-11 2009-09-17 学校法人東京理科大学 Method for producing optically active ester and method for producing optically active carboxylic acid
WO2010104034A1 (en) 2009-03-12 2010-09-16 学校法人東京理科大学 Method for producing optically active 2-hydroxy ester and novel intermediate compound
WO2012169575A1 (en) 2011-06-10 2012-12-13 学校法人東京理科大学 Method for manufacturing optically active carboxylic acid ester
JP2013039518A (en) * 2011-08-12 2013-02-28 Tokyo Univ Of Science Novel asymmetric catalyst, and method for producing optically active carboxylic acid ester, optically active alcohol and optically active carboxylic acid
WO2015115650A1 (en) * 2014-02-03 2015-08-06 学校法人東京理科大学 Method for producing optically active carboxylic acid ester
JP2015224227A (en) * 2014-05-28 2015-12-14 宇部興産株式会社 Method of producing (acetylene)dicobalt hexacarbonyl compound

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BIRMAN V.B. ET AL., ORGANIC LETTERS, vol. 8, no. 21, 2006, pages 4859 - 4861 *
BIRMAN V.B., ORGANIC LETTERS, vol. 8, no. 7, 2006, pages 1351 - 1354 *
SHIINA I. ET AL.: "The first asymmetric esterification of free carboxylic acids with racemic alcohols using benzoic anhydrides and tetramisole derivatives: an application to the kinetic resolution of secondary benzylic alcohols", TETRAHEDRON LETTERS, vol. 48, no. 47, 24 October 2007 (2007-10-24), pages 8314 - 8317, XP022313021 *
SHIINA I.: "Chikan Ansoku Kosan Musuibutsu o Mochiiru Daiinkan Oyobi Chuinkan Lacton-rui no Kosoku Gosei Hanno no Kaihatsu", JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, vol. 63, no. 1, 2005, pages 2 - 17 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5435656B2 (en) * 2008-03-11 2014-03-05 学校法人東京理科大学 Method for producing optically active ester and method for producing optically active carboxylic acid
US8115008B2 (en) 2008-03-11 2012-02-14 Tokyo University Of Science Education Foundation Administrative Organization Method for producing optically active ester and method for producing optically active carboxylic acid
WO2009113428A1 (en) * 2008-03-11 2009-09-17 学校法人東京理科大学 Method for producing optically active ester and method for producing optically active carboxylic acid
WO2010104034A1 (en) 2009-03-12 2010-09-16 学校法人東京理科大学 Method for producing optically active 2-hydroxy ester and novel intermediate compound
JP5605716B2 (en) * 2009-03-12 2014-10-15 学校法人東京理科大学 Method for producing optically active 2-hydroxyester
US8552215B2 (en) 2009-03-12 2013-10-08 Tokyo University Of Science Educational Foundation Administrative Organization Method for producing optically active 2-hydroxy ester and novel intermediate compound
WO2012169575A1 (en) 2011-06-10 2012-12-13 学校法人東京理科大学 Method for manufacturing optically active carboxylic acid ester
US9315442B2 (en) 2011-06-10 2016-04-19 Tokyo University Of Science Educational Foundation Administrative Organization Method for manufacturing optically active carboxylic acid ester
JP2013039518A (en) * 2011-08-12 2013-02-28 Tokyo Univ Of Science Novel asymmetric catalyst, and method for producing optically active carboxylic acid ester, optically active alcohol and optically active carboxylic acid
WO2015115650A1 (en) * 2014-02-03 2015-08-06 学校法人東京理科大学 Method for producing optically active carboxylic acid ester
JPWO2015115650A1 (en) * 2014-02-03 2017-03-23 学校法人東京理科大学 Method for producing optically active carboxylic acid ester
US9796640B2 (en) 2014-02-03 2017-10-24 Tokyo University Of Science Foundation Method for producing optically active carboxylic acid ester
JP2015224227A (en) * 2014-05-28 2015-12-14 宇部興産株式会社 Method of producing (acetylene)dicobalt hexacarbonyl compound

Also Published As

Publication number Publication date
JPWO2008140074A1 (en) 2010-08-05
JP5417560B2 (en) 2014-02-19

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