WO2010013809A1 - 光学活性チタンサラン化合物及びその製造方法 - Google Patents

光学活性チタンサラン化合物及びその製造方法 Download PDF

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Publication number
WO2010013809A1
WO2010013809A1 PCT/JP2009/063669 JP2009063669W WO2010013809A1 WO 2010013809 A1 WO2010013809 A1 WO 2010013809A1 JP 2009063669 W JP2009063669 W JP 2009063669W WO 2010013809 A1 WO2010013809 A1 WO 2010013809A1
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WO
WIPO (PCT)
Prior art keywords
complex
salan
optically active
active titanium
production
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2009/063669
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English (en)
French (fr)
Inventor
章一 近藤
康一郎 猿橋
健一 関
克明 宮地
松本　和弘
勗 香月
久保　卓也
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Nissan Chemical Corp
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Nissan Chemical Corp
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Filing date
Publication date
Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Publication of WO2010013809A1 publication Critical patent/WO2010013809A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
    • C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

【課題】 　不斉エポキシ化反応に有用である光学活性チタンサラン化合物及びその効率的な製造方法の提供。 【解決手段】 　不斉エポキシ化反応に有用である光学活性チタンサラン化合物をジ－μ－オキソチタンサラン錯体として単離しようとする際に、三種類の幾何異性体の混合物になることを発見した。その中で製造時の主生成分となる２つの幾何異性体の触媒性能を比較したところ、ホモキラル錯体が、擬似へテロキラル錯体よりも不斉エポキシ化反応における最終的な収率が良いことを見出した。そこで、光学活性チタンサラン化合物の製造検討で、触媒性能の良い下記式（Ａ）又は式（Ａ’）の光学活性チタンサラン化合物のホモキラル錯体を効率良く生成させ、触媒性能の劣る擬似へテロキラル錯体をできる限り排除できる製造技術を検討した結果、製造に際してニトリル系有機溶媒、エーテル系有機溶媒又は芳香族炭化水素系有機溶媒を用いることで、光学活性チタンサラン化合物のホモキラル錯体を高い単離収率及び高い化学純度で効率的に製造できる技術を確立した。
PCT/JP2009/063669 2008-07-31 2009-07-31 光学活性チタンサラン化合物及びその製造方法 Ceased WO2010013809A1 (ja)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2008197725 2008-07-31
JP2008-197725 2008-07-31
JP2008-227467 2008-09-04
JP2008227467A JP2011201779A (ja) 2008-07-31 2008-09-04 光学活性チタンサラン化合物及びその製造方法

Publications (1)

Publication Number Publication Date
WO2010013809A1 true WO2010013809A1 (ja) 2010-02-04

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JP (1) JP2011201779A (ja)
WO (1) WO2010013809A1 (ja)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102408344A (zh) * 2011-08-01 2012-04-11 温州大学 一类手性溶剂化试剂
CN107995909A (zh) * 2015-04-27 2018-05-04 尤尼威蒂恩技术有限责任公司 双(氨基苯基苯酚)配位体以及由其制备的过渡金属化合物
CN118047738A (zh) * 2024-03-19 2024-05-17 扬州大学 一种(1r,2s,3r)-1-((r)-环氧乙烷-2-基)-4-戊烯-1,3-二醇的不对称合成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006087874A1 (ja) * 2005-02-18 2006-08-24 Japan Science And Technology Agency 光学活性なエポキシ化合物の製造方法、並びに該方法に用いる錯体及びその製造方法
WO2007105658A1 (ja) * 2006-03-10 2007-09-20 Nissan Chemical Industries, Ltd. 光学活性クロメンオキシド化合物の製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006087874A1 (ja) * 2005-02-18 2006-08-24 Japan Science And Technology Agency 光学活性なエポキシ化合物の製造方法、並びに該方法に用いる錯体及びその製造方法
WO2007105658A1 (ja) * 2006-03-10 2007-09-20 Nissan Chemical Industries, Ltd. 光学活性クロメンオキシド化合物の製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MATSUMOTO ET AL.: "Construction of Pseudo- Heterochiral and Homo chiral Di-p-oxotitanium (Schiff base) Dimers and Enantioselec tive Epoxidation Using Aqueous Hydrogen Peroxide", ANGEWANDTE CHE MIE INTERNATIONAL EDITION, vol. 44, no. 31, 2005, pages 4935 - 4939 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102408344A (zh) * 2011-08-01 2012-04-11 温州大学 一类手性溶剂化试剂
CN107995909A (zh) * 2015-04-27 2018-05-04 尤尼威蒂恩技术有限责任公司 双(氨基苯基苯酚)配位体以及由其制备的过渡金属化合物
US10696641B2 (en) 2015-04-27 2020-06-30 Univation Technologies, Llc Bis(aminophenylphenol) ligands and transition metal catalysts prepared therefrom
CN107995909B (zh) * 2015-04-27 2020-12-01 尤尼威蒂恩技术有限责任公司 双(氨基苯基苯酚)配位体以及由其制备的过渡金属化合物
CN118047738A (zh) * 2024-03-19 2024-05-17 扬州大学 一种(1r,2s,3r)-1-((r)-环氧乙烷-2-基)-4-戊烯-1,3-二醇的不对称合成方法

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