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WO2004076464A3 - Optically active phosphites and phosphoramidites and their use in asymmetric reactions - Google Patents

Optically active phosphites and phosphoramidites and their use in asymmetric reactions Download PDF

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Publication number
WO2004076464A3
WO2004076464A3 PCT/US2004/003367 US2004003367W WO2004076464A3 WO 2004076464 A3 WO2004076464 A3 WO 2004076464A3 US 2004003367 W US2004003367 W US 2004003367W WO 2004076464 A3 WO2004076464 A3 WO 2004076464A3
Authority
WO
WIPO (PCT)
Prior art keywords
optically active
phosphoramidites
phosphites
asymmetric reactions
asymmetric
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/US2004/003367
Other languages
French (fr)
Other versions
WO2004076464A2 (en
Inventor
Iwao Ojima
Masaki Takai
Takayoshi Takahashi
Hisao Urata
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Chemical Corp
Research Foundation of the State University of New York
Original Assignee
Mitsubishi Chemical Corp
Research Foundation of the State University of New York
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 Mitsubishi Chemical Corp, Research Foundation of the State University of New York filed Critical Mitsubishi Chemical Corp
Publication of WO2004076464A2 publication Critical patent/WO2004076464A2/en
Publication of WO2004076464A3 publication Critical patent/WO2004076464A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C07C45/505—Asymmetric hydroformylation
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/242—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyaryl compounds
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/60—Quinoline or hydrogenated quinoline ring systems
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657154—Cyclic esteramides of oxyacids of phosphorus
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Novel optically active ligands which are mondentate phosphites and phosphoramidites, and bidentate phosphites and phosphoramidites; optically active catalysts comprising a reaction mixture of the ligand and a transition metal or its compound; and processes of using the optically active catalysts to produce optically active compounds.
PCT/US2004/003367 2003-02-27 2004-02-27 Optically active phosphites and phosphoramidites and their use in asymmetric reactions Ceased WO2004076464A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PCT/US2003/005790 WO2004078766A1 (en) 2003-02-27 2003-02-27 Optically active phosphites and phosphoramides bearing biphenol skeletons with axial chirality, and their use in catalytic asymmetric reactions
USPCT/US03/05790 2003-02-27

Publications (2)

Publication Number Publication Date
WO2004076464A2 WO2004076464A2 (en) 2004-09-10
WO2004076464A3 true WO2004076464A3 (en) 2004-12-16

Family

ID=32925338

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/US2003/005790 Ceased WO2004078766A1 (en) 2003-02-27 2003-02-27 Optically active phosphites and phosphoramides bearing biphenol skeletons with axial chirality, and their use in catalytic asymmetric reactions
PCT/US2004/003367 Ceased WO2004076464A2 (en) 2003-02-27 2004-02-27 Optically active phosphites and phosphoramidites and their use in asymmetric reactions

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/US2003/005790 Ceased WO2004078766A1 (en) 2003-02-27 2003-02-27 Optically active phosphites and phosphoramides bearing biphenol skeletons with axial chirality, and their use in catalytic asymmetric reactions

Country Status (2)

Country Link
AU (1) AU2003219901A1 (en)
WO (2) WO2004078766A1 (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10349343A1 (en) 2003-10-23 2005-06-02 Basf Ag Stabilization of hydroformylation catalysts based on phosphoramidite ligands
DE102005015893A1 (en) 2005-04-06 2006-10-12 Basf Ag Improved process for the preparation of biphenols from monophenols
JP2007302597A (en) * 2006-05-10 2007-11-22 Mitsubishi Chemicals Corp Method for producing allyl compounds
CN100430139C (en) * 2006-06-09 2008-11-05 中国科学院上海有机化学研究所 Application of Substituted Bidentate Phosphoramidite Ligands with Binaphthol Skeleton in Olefin Hydroformylation
JP5056226B2 (en) * 2007-07-12 2012-10-24 三菱化学株式会社 Method for producing allyl compound derivative
SG11201600441QA (en) * 2013-07-23 2016-02-26 Evonik Degussa Gmbh Phosphoramidite derivatives in the hydroformylation of unsaturated compounds
DE102013214378A1 (en) * 2013-07-23 2015-01-29 Evonik Industries Ag Phosphoramidite derivatives in the hydroformylation of olefin-containing mixtures
SG11201600438VA (en) * 2013-07-23 2016-02-26 Evonik Degussa Gmbh Phosphoramidite derivatives in the hydroformylation of unsaturated compounds
CN103509056B (en) * 2013-10-10 2016-07-13 中国海洋石油总公司 A kind of microwave synthesis method of diphosphite three (2,2 '-xenol) ester
EP3029049A1 (en) * 2014-12-04 2016-06-08 Evonik Degussa GmbH Monophosphites with a menthol
EP3037427B1 (en) * 2014-12-04 2016-11-23 Evonik Degussa GmbH Monophosphites with a naphthol
ES2670512T3 (en) * 2014-12-04 2018-05-30 Evonik Degussa Gmbh 9-antrol monophosphite esters as ligands for hydroformylation catalysts
EP3029054B1 (en) * 2014-12-04 2016-11-23 Evonik Degussa GmbH Phosphoramidites containing a phenyl-phenyl unit or a phenyl-naphthyl unit
ES2626367T3 (en) 2014-12-04 2017-07-24 Evonik Degussa Gmbh Monophosphites that have an asymmetric biaryl component
CN104610363B (en) * 2015-01-23 2018-04-10 中山大学 Phosphorous amide ligand and its preparation method and application
EP3147289B1 (en) * 2015-09-22 2017-11-22 Evonik Degussa GmbH Monophosphites comprising a partially hydrated binol derivative
CN106699713B (en) * 2015-11-17 2020-04-10 万华化学集团股份有限公司 Method for preparing 2-hydroxy-4-methyl tetrahydropyran
CN108586529A (en) * 2018-03-06 2018-09-28 上海交通大学 A kind of chipal compounds and the preparation method and application thereof containing biphenyl backbone
JP6798636B1 (en) * 2019-10-31 2020-12-09 三菱ケミカル株式会社 Method for producing sodium salt of phenolic compound
CN113713862B (en) * 2020-05-26 2023-04-11 中国科学院大连化学物理研究所 Co-based multi-phase catalyst for olefin hydroformylation reaction, preparation and application thereof
CN114075245B (en) * 2020-08-18 2024-06-04 中国石油化工股份有限公司 Bidentate phosphite ligand, preparation method and application thereof
CN115490732B (en) * 2022-09-30 2023-04-25 安徽泽升科技有限公司 Synthesis method of chiral biphenyl diol catalyst
EP4484437A1 (en) * 2023-06-27 2025-01-01 Evonik Oxeno GmbH & Co. KG Process for the preparation of diphosphites

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002004466A2 (en) * 2000-07-07 2002-01-17 Dsm N.V. Catalyst for asymmetric (transfer) hydrogenation
WO2002040491A1 (en) * 2000-11-17 2002-05-23 The Penn State Research Foundation Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catayltic reactions

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN187044B (en) * 1995-01-27 2002-01-05 Du Pont
DE19717359B4 (en) * 1996-04-30 2014-10-30 Mitsubishi Chemical Corp. Bisphosphite compounds and process for their preparation
US5952530A (en) * 1998-02-02 1999-09-14 Union Carbide Chemicals & Plastics Technology Corporation Separation processes
JP2000053688A (en) * 1998-08-05 2000-02-22 Mitsubishi Chemicals Corp Method for producing polydentate phosphite compound
DE60031697T2 (en) * 1999-09-20 2007-10-25 Invista Technologies S.A.R.L., Wilmington Multidentate phosphite ligands, and catalytic compositions containing them

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002004466A2 (en) * 2000-07-07 2002-01-17 Dsm N.V. Catalyst for asymmetric (transfer) hydrogenation
WO2002040491A1 (en) * 2000-11-17 2002-05-23 The Penn State Research Foundation Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catayltic reactions

Also Published As

Publication number Publication date
WO2004078766A1 (en) 2004-09-16
AU2003219901A1 (en) 2004-09-28
WO2004076464A2 (en) 2004-09-10
AU2003219901A8 (en) 2004-09-28

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