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

Info

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
Application number
PCT/US2004/003367
Other languages
French (fr)
Other versions
WO2004076464A2 (en
Inventor
Iwao Ojima
Masaki Takai
Takayoshi Takahashi
Hisao Urata
Original Assignee
Mitsubishi Chem Corp
Univ New York State Res Found
Iwao Ojima
Masaki Takai
Takayoshi Takahashi
Hisao Urata
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 Chem Corp, Univ New York State Res Found, Iwao Ojima, Masaki Takai, Takayoshi Takahashi, Hisao Urata filed Critical Mitsubishi Chem Corp
Publication of WO2004076464A2 publication Critical patent/WO2004076464A2/en
Publication of WO2004076464A3 publication Critical patent/WO2004076464A3/en

Links

Classifications

    • 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 System
    • 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 System
    • 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 System
    • 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 System
    • 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 System
    • 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 System
    • 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 System
    • 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

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 WO2004076464A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
USPCT/US03/05790 2003-02-27
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

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 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 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 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 (22)

* 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 compound
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 amido phosphite ligand on binaphthol skeleton in hydroformylation of olefin
JP5056226B2 (en) * 2007-07-12 2012-10-24 三菱化学株式会社 Method for producing allyl compound derivative
WO2015011145A1 (en) * 2013-07-23 2015-01-29 Evonik Industries Ag Phosphoramidite derivatives in the hydroformylation of unsaturated compounds
US20160168071A1 (en) * 2013-07-23 2016-06-16 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
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
EP3029052B1 (en) * 2014-12-04 2018-02-28 Evonik Degussa GmbH 9-Anthrol-monophosphit Esters as Ligands for Hydroformylation Catalysts
EP3101022B1 (en) * 2014-12-04 2018-02-28 Evonik Degussa GmbH Monophosphites having an unsymmetric biaryl unit
EP3029054B1 (en) * 2014-12-04 2016-11-23 Evonik Degussa GmbH Phosphoramidites containing a phenyl-phenyl unit or a phenyl-naphthyl unit
EP3037427B1 (en) * 2014-12-04 2016-11-23 Evonik Degussa GmbH Monophosphites with a naphthol
EP3031814B1 (en) * 2014-12-04 2016-11-23 Evonik Degussa GmbH Monophosphites with a menthol
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
CN114075245A (en) * 2020-08-18 2022-02-22 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

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 Production of multidentate phosphite compound
BR0014567A (en) * 1999-09-20 2002-06-18 Du Pont Hydrocyanation process, multidentate phosphite binder and catalyst composition

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

Similar Documents

Publication Publication Date Title
WO2004076464A3 (en) Optically active phosphites and phosphoramidites and their use in asymmetric reactions
WO2004101581A3 (en) Nitrogen-containing monodentate phosphines and their use in catalysis
WO2003016321A3 (en) Novel phosphite compounds and novel phosphite metal complexes
WO2005082819A3 (en) Metal complexes for use in olefin metathesis and atom group transfer reactions
MXPA04001348A (en) Novel phosphite compounds and the metal complexes thereof.
WO2007022945A3 (en) Multicoordinated metal complexes for use in metathesis reactions
WO2009094201A3 (en) Catalysts for metathesis reactons including enantioselective olefin metathesis, and related methods
DK1097158T3 (en) Ligands for metals and metal-catalyzed methods
ATE480548T1 (en) PHOSPHANE LIGANDS CONTAINING ADAMANTYL GROUPS, THEIR PREPARATION AND THEIR USE IN CATALYTIC REACTIONS
BR9709790A (en) Asymmetric synthesis catalyzed by transition metal complexes with cyclic chiral phosphine binders
WO2007078859A3 (en) Tetraphosphorus ligands for catalytic hydroformylation and related reactions
WO2003045555A3 (en) Process for the preparation of a nickel/phosphorus ligand catalyst for olefin hydrocyanation
AU2002365409A1 (en) Supported bis(phosphorus)ligands and their use in the catalysis
AR048153A1 (en) CONTINUOUS PROCEDURE FOR THE PREPARATION OF LINEAR PENTENONITRILS
EP1954703A4 (en) Novel dinuclear transition metal compound, catalyst composition comprising the same, method of preparing olefin polymer, and olefin polymer produced using the method
WO2005073166A3 (en) Method for the production of pentene nitriles from n-butane
WO2004094442A3 (en) Asymmetric catalysts prepared from optically active bisphosphites bridged by achiral diols
MY130628A (en) Phosphorus containing ligands for metathesis catalysts
IN2006CH00378A (en) Asymmetric urea compound and process for producing asymmetric compound by asymmetric conjugate addition reaction with the same as catalyst
CA2534324A1 (en) Ruthenium metathesis catalysts
EP1724251A4 (en) Process for production of optically active hydroxymethylated compounds
ATE473050T1 (en) RECYCLABLE CHIRAL METATHESIS CATALYSTS
WO2006081384A3 (en) Heterogeneous copper catalysts
ATE271059T1 (en) CYCLOALIPHATIC-AROMATIC DIPHOSPHINS AND THEIR USE IN CATALYSIS
WO2007020221A3 (en) Amino-phosphinoalkyl-ferrocenes and their use as ligands in catalysts for asymmetric reactions

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): BW GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase