WO2008140074A1 - Procédé de production d'ester d'acide carboxylique optiquement actif - Google Patents

Procédé de production d'ester d'acide carboxylique optiquement actif 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
English (en)
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/ja
Publication of WO2008140074A1 publication Critical patent/WO2008140074A1/fr

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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

L'invention concerne un procédé de production d'un ester d'acide carboxylique optiquement actif directement à partir d'un alcool racémique secondaire et d'un acide carboxylique. L'invention concerne également un procédé de décomposition optique d'un alcool racémique secondaire dans le même procédé que le procédé mentionné ci-dessus. L'un des énantiomères d'un alcool racémique secondaire et un acide carboxylique sont soumis à une condensation déshydratante en présence d'anhydride benzoïque ou d'un dérivé de celui-ci en utilisant du (-)-tétramisole, du (+)-tétramisole, du (-)-benzotétramisole, du (+)-benzotétramisole ou analogue comme catalyseur d'estérification asymétrique, produisant ainsi un ester d'acide carboxylique optiquement actif ; et l'autre des énantiomères qui n'a pas réagi, est décomposé optiquement.
PCT/JP2008/058743 2007-05-14 2008-05-12 Procédé de production d'ester d'acide carboxylique optiquement actif WO2008140074A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2009514165A JP5417560B2 (ja) 2007-05-14 2008-05-12 光学活性カルボン酸エステルを製造する方法

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 (fr) 2008-11-20

Family

ID=40002264

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/058743 WO2008140074A1 (fr) 2007-05-14 2008-05-12 Procédé de production d'ester d'acide carboxylique optiquement actif

Country Status (2)

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

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009113428A1 (fr) * 2008-03-11 2009-09-17 学校法人東京理科大学 Procédé de fabrication d'un ester optiquement actif et procédé de fabrication d'un acide carboxylique optiquement actif
WO2010104034A1 (fr) 2009-03-12 2010-09-16 学校法人東京理科大学 Procédé de production d'un 2-hydroxy ester optiquement actif et d'un nouveau composé intermédiaire
WO2012169575A1 (fr) 2011-06-10 2012-12-13 学校法人東京理科大学 Procédé pour fabriquer un ester d'acide carboxylique optiquement actif
JP2013039518A (ja) * 2011-08-12 2013-02-28 Tokyo Univ Of Science 新規不斉触媒、並びに光学活性カルボン酸エステル、光学活性アルコール、及び光学活性カルボン酸の製造方法
WO2015115650A1 (fr) * 2014-02-03 2015-08-06 学校法人東京理科大学 Procédé de fabrication d'un ester d'acide carboxylique optiquement actif
JP2015224227A (ja) * 2014-05-28 2015-12-14 宇部興産株式会社 （アセチレン）ジコバルトヘキサカルボニル化合物の製造方法

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 (ja) * 2008-03-11 2014-03-05 学校法人東京理科大学 光学活性エステルの製造方法及び光学活性カルボン酸の製造方法
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 (fr) * 2008-03-11 2009-09-17 学校法人東京理科大学 Procédé de fabrication d'un ester optiquement actif et procédé de fabrication d'un acide carboxylique optiquement actif
WO2010104034A1 (fr) 2009-03-12 2010-09-16 学校法人東京理科大学 Procédé de production d'un 2-hydroxy ester optiquement actif et d'un nouveau composé intermédiaire
JP5605716B2 (ja) * 2009-03-12 2014-10-15 学校法人東京理科大学 光学活性２−ヒドロキシエステルの製造方法
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 (fr) 2011-06-10 2012-12-13 学校法人東京理科大学 Procédé pour fabriquer un ester d'acide carboxylique optiquement actif
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 (ja) * 2011-08-12 2013-02-28 Tokyo Univ Of Science 新規不斉触媒、並びに光学活性カルボン酸エステル、光学活性アルコール、及び光学活性カルボン酸の製造方法
WO2015115650A1 (fr) * 2014-02-03 2015-08-06 学校法人東京理科大学 Procédé de fabrication d'un ester d'acide carboxylique optiquement actif
JPWO2015115650A1 (ja) * 2014-02-03 2017-03-23 学校法人東京理科大学 光学活性カルボン酸エステルの製造方法
US9796640B2 (en) 2014-02-03 2017-10-24 Tokyo University Of Science Foundation Method for producing optically active carboxylic acid ester
JP2015224227A (ja) * 2014-05-28 2015-12-14 宇部興産株式会社 （アセチレン）ジコバルトヘキサカルボニル化合物の製造方法

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

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