FR2812638B1 - Utilisation de diphosphines chirales comme ligands optiquement actifs pour la preparation de complexes diphosphino-metalliques, les complexes ainsi obtenus et les procedes de catalyse asymetrique les mettant en oeuvre - Google Patents

Utilisation de diphosphines chirales comme ligands optiquement actifs pour la preparation de complexes diphosphino-metalliques, les complexes ainsi obtenus et les procedes de catalyse asymetrique les mettant en oeuvre

Info

Publication number
FR2812638B1
FR2812638B1 FR0010269A FR0010269A FR2812638B1 FR 2812638 B1 FR2812638 B1 FR 2812638B1 FR 0010269 A FR0010269 A FR 0010269A FR 0010269 A FR0010269 A FR 0010269A FR 2812638 B1 FR2812638 B1 FR 2812638B1
Authority
FR
France
Prior art keywords
complexes
diphosphino
preparation
optically active
same
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.)
Expired - Fee Related
Application number
FR0010269A
Other languages
English (en)
Other versions
FR2812638A1 (fr
Inventor
Michel Bulliard
Blandine Laboue
Sonia Roussiasse
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.)
Zach System SA
Original Assignee
PPG Sipsy SAS
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
Priority to FR0010269A priority Critical patent/FR2812638B1/fr
Application filed by PPG Sipsy SAS filed Critical PPG Sipsy SAS
Priority to CA002417836A priority patent/CA2417836A1/fr
Priority to PCT/FR2001/002550 priority patent/WO2002012253A1/fr
Priority to IL15426301A priority patent/IL154263A0/xx
Priority to BR0112970-8A priority patent/BR0112970A/pt
Priority to CNA018167381A priority patent/CN1468248A/zh
Priority to AU2001282264A priority patent/AU2001282264A1/en
Priority to JP2002518228A priority patent/JP2004505985A/ja
Priority to EP01960868A priority patent/EP1305324A1/fr
Publication of FR2812638A1 publication Critical patent/FR2812638A1/fr
Priority to US10/356,233 priority patent/US6794525B2/en
Application granted granted Critical
Publication of FR2812638B1 publication Critical patent/FR2812638B1/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C07F15/0046—Ruthenium compounds
    • C07F15/0053—Ruthenium 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5027—Polyphosphines
    • 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
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/52—Isomerisation reactions
    • 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
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • 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
    • B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0202—Polynuclearity
    • B01J2531/0208—Bimetallic complexes, i.e. comprising one or more units of two metals, with metal-metal bonds but no all-metal (M)n rings, e.g. Cr2(OAc)4
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • 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
    • B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
    • B01J2531/26—Zinc
    • 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
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/31—Aluminium
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/42—Tin
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/46—Titanium
    • 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
    • B01J2531/821—Ruthenium
    • 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
    • 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
    • B01J2531/827—Iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
FR0010269A 2000-08-03 2000-08-03 Utilisation de diphosphines chirales comme ligands optiquement actifs pour la preparation de complexes diphosphino-metalliques, les complexes ainsi obtenus et les procedes de catalyse asymetrique les mettant en oeuvre Expired - Fee Related FR2812638B1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
FR0010269A FR2812638B1 (fr) 2000-08-03 2000-08-03 Utilisation de diphosphines chirales comme ligands optiquement actifs pour la preparation de complexes diphosphino-metalliques, les complexes ainsi obtenus et les procedes de catalyse asymetrique les mettant en oeuvre
EP01960868A EP1305324A1 (fr) 2000-08-03 2001-08-03 Utilisation de diphosphines chirales comme ligands optiquement actifs
IL15426301A IL154263A0 (en) 2000-08-03 2001-08-03 Use of chiral diphosphines as optically active ligands
BR0112970-8A BR0112970A (pt) 2000-08-03 2001-08-03 Utilização de difosfinas quirais como ligantes opticamente ativos
CNA018167381A CN1468248A (zh) 2000-08-03 2001-08-03 手性二膦作为旋光配体的应用
AU2001282264A AU2001282264A1 (en) 2000-08-03 2001-08-03 Use of chiral diphosphines as optically active ligands
CA002417836A CA2417836A1 (fr) 2000-08-03 2001-08-03 Utilisation de diphosphines chirales comme ligands optiquement actifs
PCT/FR2001/002550 WO2002012253A1 (fr) 2000-08-03 2001-08-03 Utilisation de diphosphines chirales comme ligands optiquement actifs
JP2002518228A JP2004505985A (ja) 2000-08-03 2001-08-03 光学活性をもつリガンドとしてのキラルジホスフィンの利用
US10/356,233 US6794525B2 (en) 2000-08-03 2003-01-31 Optically active chiral diphosphine ligands

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0010269A FR2812638B1 (fr) 2000-08-03 2000-08-03 Utilisation de diphosphines chirales comme ligands optiquement actifs pour la preparation de complexes diphosphino-metalliques, les complexes ainsi obtenus et les procedes de catalyse asymetrique les mettant en oeuvre

Publications (2)

Publication Number Publication Date
FR2812638A1 FR2812638A1 (fr) 2002-02-08
FR2812638B1 true FR2812638B1 (fr) 2003-04-25

Family

ID=8853276

Family Applications (1)

Application Number Title Priority Date Filing Date
FR0010269A Expired - Fee Related FR2812638B1 (fr) 2000-08-03 2000-08-03 Utilisation de diphosphines chirales comme ligands optiquement actifs pour la preparation de complexes diphosphino-metalliques, les complexes ainsi obtenus et les procedes de catalyse asymetrique les mettant en oeuvre

Country Status (10)

Country Link
US (1) US6794525B2 (fr)
EP (1) EP1305324A1 (fr)
JP (1) JP2004505985A (fr)
CN (1) CN1468248A (fr)
AU (1) AU2001282264A1 (fr)
BR (1) BR0112970A (fr)
CA (1) CA2417836A1 (fr)
FR (1) FR2812638B1 (fr)
IL (1) IL154263A0 (fr)
WO (1) WO2002012253A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2401864B (en) * 2003-05-21 2007-11-14 Phoenix Chemicals Ltd Process and catalytic composition
AU2007233814B2 (en) * 2006-04-03 2012-08-16 F. Hoffmann-La Roche Ag Process for preparation of enantiomerically enriched cyclic beta-aryl or heteroaryl carboxylic acids
WO2010069793A1 (fr) 2008-12-16 2010-06-24 F. Hoffmann-La Roche Ag Méthode de préparation d'acides pyrrolidine-3-carboxyliques
FR2952638A1 (fr) 2009-11-17 2011-05-20 Univ Strasbourg Procede de phosphination catalytique double ou triple de composes di, tri ou tetrahalobiaryles, intermediaires employes, composes obtenus et leurs utilisations
CN103145557B (zh) * 2013-03-27 2015-06-03 石家庄手性化学有限公司 一种光学纯度的s-4-氯-3-羟基丁酸乙酯的制备方法
CN108690074A (zh) * 2018-05-15 2018-10-23 东华大学 一种兼有磷中心手性和联萘轴手性的双膦手性化合物及其制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59309570D1 (de) * 1992-01-31 1999-06-17 Hoffmann La Roche Diphosphinliganden
DE59308424D1 (de) * 1992-01-31 1998-05-28 Hoffmann La Roche Diphosphinliganden
ES2130321T3 (es) * 1993-10-08 1999-07-01 Hoffmann La Roche Compuestos de fosforo opticamente activos.
DE69908889T2 (de) * 1998-11-19 2004-05-06 Solvias Ag Chirale Diphenyldiphosphine und d-8 Metall-Komplexe davon
AU7590600A (en) * 1999-09-20 2001-04-24 Penn State Research Foundation, The Chiral phosphines, transition metal complexes thereof and uses thereof in asymmetric reactions

Also Published As

Publication number Publication date
AU2001282264A1 (en) 2002-02-18
JP2004505985A (ja) 2004-02-26
EP1305324A1 (fr) 2003-05-02
BR0112970A (pt) 2003-06-24
CA2417836A1 (fr) 2002-02-14
WO2002012253A1 (fr) 2002-02-14
FR2812638A1 (fr) 2002-02-08
CN1468248A (zh) 2004-01-14
US20030195369A1 (en) 2003-10-16
US6794525B2 (en) 2004-09-21
IL154263A0 (en) 2003-09-17

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