WO2010013809A1 - Optically active titanium-salan compounds and process for production thereof - Google Patents

Optically active titanium-salan compounds and process for production thereof 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
Authority
WO
WIPO (PCT)
Prior art keywords
complex
salan
optically active
active titanium
production
Prior art date
Application number
PCT/JP2009/063669
Other languages
French (fr)
Japanese (ja)
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
Original Assignee
日産化学工業株式会社
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 日産化学工業株式会社 filed Critical 日産化学工業株式会社
Publication of WO2010013809A1 publication Critical patent/WO2010013809A1/en

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Classifications

    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)

Abstract

Provided are optically active titanium-salan compounds useful for asymmetric epoxidation and a process for efficient production thereof. In isolating an optically active titanium-salan compound useful for asymmetric epoxidation as a di-μ-oxo titanium salan complex, the complex has been found to be present as a mixture of three geometrical isomers.  By comparing the catalytic performances of the major two of the three geometrical isomers, it has been found that the homochiral complex gives a higher ultimate yield than that of the pseudo-heterochiral complex in asymmetric epoxidation.  In the production of optically active titanium -salan compounds, therefore, a study has been made on production technique which enables efficient formation of a homochiral complex of an optically active titanium-salan compound and which makes it possible to exclude a pseudo-heterochiral complex of an optically active titanium-salan compound as completely as possible, the homochiral complex being represented by the general formula (A) or (A’) and being superior to the pseudo-heterochiral complex in catalytic performance.  As a result, a technique for producing a homochiral complex of an optically active titanium-salan compound efficiently in a high isolation yield and with high chemical purity has been established by using a nitrile-, ether-, or aromatic hydrocarbon-type organic solvent in the production of the titanium-salan compound.
PCT/JP2009/063669 2008-07-31 2009-07-31 Optically active titanium-salan compounds and process for production thereof WO2010013809A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2008-197725 2008-07-31
JP2008197725 2008-07-31
JP2008-227467 2008-09-04
JP2008227467A JP2011201779A (en) 2008-07-31 2008-09-04 Optically active titanium-salan compound and method for producing the same

Publications (1)

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

Family

ID=41610503

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2009/063669 WO2010013809A1 (en) 2008-07-31 2009-07-31 Optically active titanium-salan compounds and process for production thereof

Country Status (2)

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JP (1) JP2011201779A (en)
WO (1) WO2010013809A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102408344A (en) * 2011-08-01 2012-04-11 温州大学 Chiral solvating agents
CN107995909A (en) * 2015-04-27 2018-05-04 尤尼威蒂恩技术有限责任公司 Double (aminophenyl phenol) ligands and transistion metal compound prepared therefrom

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006087874A1 (en) * 2005-02-18 2006-08-24 Japan Science And Technology Agency Process for producing optically active epoxy compound, complex for use in the process, and process for producing the same
WO2007105658A1 (en) * 2006-03-10 2007-09-20 Nissan Chemical Industries, Ltd. Process for producing optically active chromene oxide compound

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006087874A1 (en) * 2005-02-18 2006-08-24 Japan Science And Technology Agency Process for producing optically active epoxy compound, complex for use in the process, and process for producing the same
WO2007105658A1 (en) * 2006-03-10 2007-09-20 Nissan Chemical Industries, Ltd. Process for producing optically active chromene oxide compound

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 (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102408344A (en) * 2011-08-01 2012-04-11 温州大学 Chiral solvating agents
CN107995909A (en) * 2015-04-27 2018-05-04 尤尼威蒂恩技术有限责任公司 Double (aminophenyl phenol) ligands and transistion metal compound prepared therefrom
US10696641B2 (en) 2015-04-27 2020-06-30 Univation Technologies, Llc Bis(aminophenylphenol) ligands and transition metal catalysts prepared therefrom
CN107995909B (en) * 2015-04-27 2020-12-01 尤尼威蒂恩技术有限责任公司 Bis (aminophenylphenol) ligands and transition metal compounds prepared therefrom

Also Published As

Publication number Publication date
JP2011201779A (en) 2011-10-13

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