[go: up one dir, main page]

WO2005047299A3 - Chirale di- und triphosphite - Google Patents

Chirale di- und triphosphite Download PDF

Info

Publication number
WO2005047299A3
WO2005047299A3 PCT/DE2004/002493 DE2004002493W WO2005047299A3 WO 2005047299 A3 WO2005047299 A3 WO 2005047299A3 DE 2004002493 W DE2004002493 W DE 2004002493W WO 2005047299 A3 WO2005047299 A3 WO 2005047299A3
Authority
WO
WIPO (PCT)
Prior art keywords
chiral
triphosphites
transition metal
bridged
compounds
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/DE2004/002493
Other languages
English (en)
French (fr)
Other versions
WO2005047299A2 (de
Inventor
Manfred Theodor Reetz
Andreas Meiswinkel
Gerlinde Mehler
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.)
Studiengesellschaft Kohle gGmbH
Original Assignee
Studiengesellschaft Kohle gGmbH
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 Studiengesellschaft Kohle gGmbH filed Critical Studiengesellschaft Kohle gGmbH
Priority to EP04802710A priority Critical patent/EP1689761A2/de
Priority to CA002546218A priority patent/CA2546218A1/en
Priority to JP2006538651A priority patent/JP2007512245A/ja
Publication of WO2005047299A2 publication Critical patent/WO2005047299A2/de
Publication of WO2005047299A3 publication Critical patent/WO2005047299A3/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073—Rhodium compounds
    • C07F15/008—Rhodium compounds without a metal-carbon linkage
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • B01J31/1855—Triamide derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • B01J31/186—Mono- or diamide derivatives thereof
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073—Rhodium 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
    • C07F9/6564—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
    • C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/16—Copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Es werden chirale Di- und Triphosphite mit den allgemeinen Formeln (I) oder (II) beansprucht, die über geeignete Gruppen verbrückt sind. Die beanspruchten Verbindungen können in der asymmetrischen Übergangsmetall-Katalyse sowie als chirale Übergangsmetall-Katalysatoren eingesetzt werden.
PCT/DE2004/002493 2003-11-12 2004-11-11 Chirale di- und triphosphite Ceased WO2005047299A2 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP04802710A EP1689761A2 (de) 2003-11-12 2004-11-11 Chirale di- und triphosphite
CA002546218A CA2546218A1 (en) 2003-11-12 2004-11-11 Chiral di- and triphosphites
JP2006538651A JP2007512245A (ja) 2003-11-12 2004-11-11 キラルジ−及びトリホスファイト

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10352757A DE10352757A1 (de) 2003-11-12 2003-11-12 Chirale Di- und Triphosphite
DE10352757.5 2003-11-12

Publications (2)

Publication Number Publication Date
WO2005047299A2 WO2005047299A2 (de) 2005-05-26
WO2005047299A3 true WO2005047299A3 (de) 2005-09-09

Family

ID=34584998

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE2004/002493 Ceased WO2005047299A2 (de) 2003-11-12 2004-11-11 Chirale di- und triphosphite

Country Status (6)

Country Link
US (1) US20060224002A1 (de)
EP (1) EP1689761A2 (de)
JP (1) JP2007512245A (de)
CA (1) CA2546218A1 (de)
DE (1) DE10352757A1 (de)
WO (1) WO2005047299A2 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006052514A1 (en) * 2004-11-04 2006-05-18 Merck & Co., Inc. Asymmetric hydrogenation of enamides
DE102005025797A1 (de) * 2005-06-02 2006-12-07 Studiengesellschaft Kohle Mbh Chirale Diphosphonite als Liganden in der ruthenium-katalysierten enantioselektiven Reduktion von Ketonen, β-Ketoestern und Ketiminen
ITMI20131612A1 (it) * 2013-09-30 2015-03-31 Maurizio Benaglia Dioli bieteroaromatici e loro derivati.
CN105753906A (zh) * 2014-12-18 2016-07-13 中国科学院兰州化学物理研究所 环己二醇衍生的手性双齿亚磷酸酯配体及其制备方法和应用
DE102015207870A1 (de) * 2015-04-29 2016-11-03 Evonik Degussa Gmbh Neue Monophosphitverbindungen mit einer Sulfonatgruppe
CN105037442B (zh) * 2015-07-17 2017-05-10 华中师范大学 手性硫醚‑膦配体及制备方法及用途
CN111203277B (zh) * 2020-02-27 2022-11-18 郑州大学 手性双齿亚磷酸酯配体的应用、Conia-Ene反应催化剂和构建手性季碳中心的方法
CN112538095B (zh) * 2020-12-14 2022-08-05 万华化学集团股份有限公司 一种手性四齿配体、手性钌络合物，及制备(r)-(-)-1,3-丁二醇的方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993003839A1 (en) * 1991-08-21 1993-03-04 Union Carbide Chemicals & Plastics Technology Corporation Asymmetric syntheses
WO1996016923A1 (en) * 1994-11-25 1996-06-06 Dsm N.V. Process for the preparation of an aldehyde
WO1999006357A1 (en) * 1997-07-29 1999-02-11 E.I. Du Pont De Nemours And Company Hydrocyanation of diolefins and isomerization of nonconjugated 2-alykl-3-monoalkenenitriles
EP1008581A1 (de) * 1998-12-10 2000-06-14 Mitsubishi Chemical Corporation Verfahren zur Herstellung von Aldehyden
WO2001007156A1 (en) * 1999-07-21 2001-02-01 Uab Research Foundation Metallacrown ether catalysts for hydroformylation
US20020128501A1 (en) * 2000-11-17 2002-09-12 The Penn State Research Foundation Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catalytic reactions
WO2004094442A2 (en) * 2003-03-28 2004-11-04 Dow Global Technologies Inc. Asymmetric catalysts prepared from optically active bisphosphites bridged by achiral diols

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4374219A (en) * 1980-11-24 1983-02-15 Ciba-Geigy Corporation Alkanolamine ester of 1,1-biphenyl-2,2-diyl-and alkylidene-1,1-biphenyl-2,2-diyl-cyclic phosphites
US4668651A (en) * 1985-09-05 1987-05-26 Union Carbide Corporation Transition metal complex catalyzed processes
US5886235A (en) * 1995-12-06 1999-03-23 Union Carbide Chemicals & Plastics Technology Corporation. Metal-ligand complex catalyzed processes
US5892119A (en) * 1996-11-26 1999-04-06 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
DE10005794A1 (de) * 2000-02-10 2001-08-16 Basf Ag Verbindungen des Phosphors, Arsens und des Antimons
DE10023471A1 (de) * 2000-05-12 2001-11-15 Basf Ag Verfahren zur Hydroformylierung, verbrückte Phosphine und Katalysator, umfassend einen Komplex dieser verbrückten Phosphine
DE10046026A1 (de) * 2000-09-18 2002-03-28 Basf Ag Verfahren zur Hydroformylierung, Xanthen-verbrückte Liganden und Katalysator, umfassend einen Komplex dieser Liganden
DE10205702A1 (de) * 2001-02-13 2002-08-29 Basf Ag Verfahren zur Hydroformylierung, Liganden mit von Bisphenol A abgeleiteter Struktur und Katalysator, umfassend einen Komplex dieser Liganden
US6664427B1 (en) * 2002-08-29 2003-12-16 E. I. Du Pont De Nemours And Company Process for preparing aldehyde compounds

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993003839A1 (en) * 1991-08-21 1993-03-04 Union Carbide Chemicals & Plastics Technology Corporation Asymmetric syntheses
US5491266A (en) * 1991-08-21 1996-02-13 Union Carbide Chemicals & Plastics Technology Corporation Asymmetric syntheses
WO1996016923A1 (en) * 1994-11-25 1996-06-06 Dsm N.V. Process for the preparation of an aldehyde
WO1999006357A1 (en) * 1997-07-29 1999-02-11 E.I. Du Pont De Nemours And Company Hydrocyanation of diolefins and isomerization of nonconjugated 2-alykl-3-monoalkenenitriles
EP1008581A1 (de) * 1998-12-10 2000-06-14 Mitsubishi Chemical Corporation Verfahren zur Herstellung von Aldehyden
WO2001007156A1 (en) * 1999-07-21 2001-02-01 Uab Research Foundation Metallacrown ether catalysts for hydroformylation
US20020128501A1 (en) * 2000-11-17 2002-09-12 The Penn State Research Foundation Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catalytic reactions
WO2004094442A2 (en) * 2003-03-28 2004-11-04 Dow Global Technologies Inc. Asymmetric catalysts prepared from optically active bisphosphites bridged by achiral diols

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BOTTEGHI C ET AL: "Aryloxypropanoic herbicides by asymmetric hydroformylation catalyzed by rhodium carbonyl complexes modified with phosphorus ligands", JOURNAL OF MOLECULAR CATALYSIS. A, CHEMICAL, ELSEVIER, AMSTERDAM, NL, vol. 143, no. 1-3, 8 July 1999 (1999-07-08), pages 311 - 323, XP002246650, ISSN: 1381-1169 *
BUISMAN G J H ET AL: "Chiral cooperativity in diastereomeric diphosphite ligands: effects on the rhodium-catalysed enantioselective hydroformylation of styrene", ORGANOMETALLICS, WASHINGTON, DC, US, vol. 16, no. 13, 24 June 1997 (1997-06-24), pages 2929 - 2939, XP002264849, ISSN: 0276-7333 *
CHINESE SCIENCE BULLETIN , 48(20), 2188-2192 CODEN: CSBUEF; ISSN: 1001-6538, 2003 *
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; YAN, MING ET AL: "Hydroformylation of olefins catalyzed by chiral phosphite-Rh(I) complexes", XP002306937, retrieved from STN Database accession no. 2003:934162 *

Also Published As

Publication number Publication date
CA2546218A1 (en) 2005-05-26
DE10352757A1 (de) 2005-06-16
US20060224002A1 (en) 2006-10-05
EP1689761A2 (de) 2006-08-16
WO2005047299A2 (de) 2005-05-26
JP2007512245A (ja) 2007-05-17

Similar Documents

Publication Publication Date Title
WO2005037198A3 (en) Preparation of 1,7-disubstituted azabenzimidazoles as kinase inhibitors
WO2003097794A3 (en) Universal-tagged oligonucleotide primers and methods of use
WO2006120208A8 (en) Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein
WO2005094440A3 (en) Nanofiber surface based capacitors
WO2005011592A3 (en) Substituted indazole-o-glucosides
WO2005012243A3 (en) Substituted indole-o-glucosides
WO2006092213A8 (de) Pyrazolylcarboxanilide
WO2005014850A3 (en) Systems and methods for analyzing nucleic acid sequences
DE502006000218D1 (de) Verfahren zur Herstellung von SiOC-verknüpften, linearen Polydialkylsiloxan-Polyoxyalkylen-Blockcopolymeren
WO2006058700A8 (en) Acetamide compounds as fungicides
WO2007075847A3 (en) Glucokinase activators
WO2005058835A3 (en) Methods of preparing aripiprazole crystalline forms
WO2004069152A3 (en) Δ4,5 glycuronidase and uses thereof
WO2005030130A3 (en) Isoquinoline potassium channel inhibitors
WO2007014930A3 (de) Polyammonium-polysiloxancopolymere
WO2005046578A3 (en) Isoquinolinone potassium channel inhibitors
ITMI20030957A1 (it) Macchina per legatoria per la lavorazione di blocchi di libro, ad elevata precisione di funzionamento.
AU2003269835A1 (en) Mixtures of chiral monophosphorus compounds used as ligand systems for asymmetric transition metal catalysis
WO2006087120A8 (de) Pyrazolopyrimidine
WO2003000186A3 (en) Novel phenylamino-pyrimidines and uses thereof
WO2005082907A3 (de) Pyrazolopyrimidine zur bekämpfung unerwünschter mikroorganismen
EP1615946A4 (de) Proteolytische und kovalente antikörper
ZA200501431B (en) 5-Aryltetrazole compounds, compositions thereof, and uses therefor.
WO2005047299A3 (de) Chirale di- und triphosphite
WO2004075021A3 (en) Molecular modeling methods

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 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 NA 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 IS IT LU MC NL PL 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
WWE Wipo information: entry into national phase

Ref document number: 2006538651

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 2004802710

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2546218

Country of ref document: CA

WWP Wipo information: published in national office

Ref document number: 2004802710

Country of ref document: EP