WO2008078601A1 - 光学活性含フッ素カルボニル－エン生成物の製造方法 - Google Patents

光学活性含フッ素カルボニル－エン生成物の製造方法 Download PDF

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Publication number
WO2008078601A1
WO2008078601A1 PCT/JP2007/074290 JP2007074290W WO2008078601A1 WO 2008078601 A1 WO2008078601 A1 WO 2008078601A1 JP 2007074290 W JP2007074290 W JP 2007074290W WO 2008078601 A1 WO2008078601 A1 WO 2008078601A1
Authority
WO
WIPO (PCT)
Prior art keywords
optically active
containing carbonyl
reaction
active fluorine
ene product
Prior art date
Application number
PCT/JP2007/074290
Other languages
English (en)
French (fr)
Inventor
Koichi Mikami
Kohsuke Aikawa
Akihiro Ishii
Kaori Mogi
Takashi Ootsuka
Original Assignee
Central Glass Company, Limited
Tokyo Institute Of Technology
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 Central Glass Company, Limited, Tokyo Institute Of Technology filed Critical Central Glass Company, Limited
Priority to CN2007800470823A priority Critical patent/CN101583589B/zh
Priority to EP07850778.7A priority patent/EP2098501B1/en
Priority to US12/519,959 priority patent/US8278479B2/en
Publication of WO2008078601A1 publication Critical patent/WO2008078601A1/ja

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

含フッ素α－ケトエステルとアルケンを、光学活性な配位子を有する遷移金属錯体の存在下、反応させることにより、光学活性含フッ素カルボニル－エン生成物が製造される。この反応を反応溶媒の非存在下で行う態様１、この反応を比誘電率の低い溶媒中で行う態様２、この反応をハロゲン化炭化水素系の溶媒中で行う態様３がある。これら３つの態様のいずれでも光学活性含フッ素カルボニル－エン生成物を安価に製造することができる。
PCT/JP2007/074290 2006-12-26 2007-12-18 光学活性含フッ素カルボニル－エン生成物の製造方法 WO2008078601A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN2007800470823A CN101583589B (zh) 2006-12-26 2007-12-18 用于生产光学活性含氟羰基-烯产物的方法
EP07850778.7A EP2098501B1 (en) 2006-12-26 2007-12-18 Method for producing optically active fluorine-containing carbonyl-ene product
US12/519,959 US8278479B2 (en) 2006-12-26 2007-12-18 Method for producing optically active fluorine-containing carbonyl-ene product

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2006-350616 2006-12-26
JP2006350616 2006-12-26
JP2007047530 2007-02-27
JP2007-047530 2007-02-27
JP2007-108681 2007-04-17
JP2007108681A JP5090773B2 (ja) 2006-12-26 2007-04-17 光学活性含フッ素カルボニル−エン生成物の製造方法

Publications (1)

Publication Number Publication Date
WO2008078601A1 true WO2008078601A1 (ja) 2008-07-03

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/074290 WO2008078601A1 (ja) 2006-12-26 2007-12-18 光学活性含フッ素カルボニル－エン生成物の製造方法

Country Status (5)

Country Link
US (1) US8278479B2 (ja)
EP (1) EP2098501B1 (ja)
JP (1) JP5090773B2 (ja)
CN (1) CN101583589B (ja)
WO (1) WO2008078601A1 (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103664609A (zh) * 2012-09-10 2014-03-26 安徽安腾药业有限责任公司 低温不对称催化制备(r)-2-羟基-2-三氟甲基-4-甲基-4-戊烯酸乙酯的方法
CN105651873A (zh) * 2015-12-29 2016-06-08 天津市长芦化工新材料有限公司 一种三氟丙酮酸甲酯的分析测定方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002502385A (ja) * 1997-05-30 2002-01-22 シエーリング アクチエンゲゼルシヤフト ゲスターゲン及びアンドロゲン混合作用を有する非ステロイド系（複素）環式置換アシルアニリド

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6245804B1 (en) 1997-05-30 2001-06-12 Schering Aktiengesellschaft Nonsteroidal gestagens
GB0120256D0 (en) * 2001-08-21 2001-10-10 Ici Plc Catalysts
US7417056B2 (en) * 2004-11-12 2008-08-26 Schering Ag 5-substituted quinoline and isoquinoline derivatives, a process for their production and their use as anti-inflammatory agents
US20060229305A1 (en) * 2005-03-22 2006-10-12 Markus Berger Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002502385A (ja) * 1997-05-30 2002-01-22 シエーリング アクチエンゲゼルシヤフト ゲスターゲン及びアンドロゲン混合作用を有する非ステロイド系（複素）環式置換アシルアニリド

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
ANGEW. CHEM. INT. ED. (GERMANY), vol. 44, 2005, pages 7257 - 7260
J. AM. CHEM. SOC. (US), vol. 121, 1999, pages 686 - 699
J. ORG. CHEM. (US), 2006
MIKAMI K. ET AL.: "Enantioselective catalysis of carbonyl-ene and Friedel-Crafts reactions with trifluoropyruvate by 'naked' palladium (II) complexes with SEGPHOS ligands", TETRAHEDRON: ASYMMETRY, vol. 15, no. 24, 13 December 2004 (2004-12-13), pages 3885 - 3889, XP004670211 *
NATURE (UK), vol. 385, 1997, pages 613 - 615
SIMON DOHERTY; JULIAN G. KNIGHT ET AL., ASYMMETRIC PLATINUM GROUP METAL-CATALYZED CARBONYL-ENE REACTIONS: CARBON-CARBON BOND FORMATION VERSUS ISOMERIZATION
TETRAHEDRON ASYMMETRY (UK), vol. 15, 2004, pages 3885 - 3889
TETRAHEDRON LETTERS (UK), vol. 45, 2004, pages 183 - 185

Also Published As

Publication number Publication date
CN101583589A (zh) 2009-11-18
US8278479B2 (en) 2012-10-02
EP2098501B1 (en) 2017-08-23
EP2098501A4 (en) 2012-02-15
JP5090773B2 (ja) 2012-12-05
US20090312574A1 (en) 2009-12-17
EP2098501A1 (en) 2009-09-09
JP2008239593A (ja) 2008-10-09
CN101583589B (zh) 2013-05-29

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