WO2004089920A3 - Amin-substituierte diphenyldiphosphine und deren verwendung in metallkomplexen für asymmetrische synthesen - Google Patents

Amin-substituierte diphenyldiphosphine und deren verwendung in metallkomplexen für asymmetrische synthesen Download PDF

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Publication number
WO2004089920A3
WO2004089920A3 PCT/EP2004/050439 EP2004050439W WO2004089920A3 WO 2004089920 A3 WO2004089920 A3 WO 2004089920A3 EP 2004050439 W EP2004050439 W EP 2004050439W WO 2004089920 A3 WO2004089920 A3 WO 2004089920A3
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Prior art keywords
metal complexes
amine
diphenyldiphosphines
substituted
asymmetric syntheses
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PCT/EP2004/050439
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English (en)
French (fr)
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WO2004089920A8 (de
WO2004089920A2 (de
Inventor
Benoit Pugin
Pierre Martin
Markus Mueller
Frederic Naud
Felix Spindler
Marc Thommen
Gianpietro Melone
Martin Kesselgruber
Original Assignee
Solvias Ag
Benoit Pugin
Pierre Martin
Markus Mueller
Frederic Naud
Felix Spindler
Marc Thommen
Gianpietro Melone
Martin Kesselgruber
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Application filed by Solvias Ag, Benoit Pugin, Pierre Martin, Markus Mueller, Frederic Naud, Felix Spindler, Marc Thommen, Gianpietro Melone, Martin Kesselgruber filed Critical Solvias Ag
Priority to EP04741445A priority Critical patent/EP1611114A2/de
Priority to JP2006505522A priority patent/JP2006523654A/ja
Priority to US10/552,066 priority patent/US7589196B2/en
Priority to CA002521635A priority patent/CA2521635A1/en
Publication of WO2004089920A2 publication Critical patent/WO2004089920A2/de
Publication of WO2004089920A3 publication Critical patent/WO2004089920A3/de
Publication of WO2004089920A8 publication Critical patent/WO2004089920A8/de

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00Asymmetric syntheses
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18Catalysts 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
    • B01J31/1845Catalysts 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
    • B01J31/1865Phosphonites (RP(OR)2), their isomeric phosphinates (R2(RO)P=O) and RO-substitution derivatives thereof
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18Catalysts 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
    • B01J31/1845Catalysts 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
    • B01J31/1875Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24Phosphines, 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
    • B01J31/2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409Cyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D265/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/341,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/361,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033Iridium compounds
    • CCHEMISTRY; METALLURGY
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    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073Rhodium compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073Rhodium compounds
    • C07F15/008Rhodium compounds without a metal-carbon linkage
    • CCHEMISTRY; METALLURGY
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    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
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    • C07F9/50Organo-phosphines
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    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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    • C07F9/65335Six-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32Addition reactions to C=C or C-C triple bonds
    • B01J2231/323Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
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    • B01J2231/60Reduction reactions, e.g. hydrogenation
    • B01J2231/64Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
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    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J2531/82Metals of the platinum group
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    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
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    • B01J2531/82Metals of the platinum group
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
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  • Chemical Kinetics & Catalysis (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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1,1'-Diphenyl-2,2'-diphosphine mit wenigstens einem Aminsubstituenten in Parastellung zur Phosphingruppe mit den Formeln sind Liganden für Metallkomplexe, die als Katalysatoren für asymmetrische Anlagerungsreaktionen von prochiralen organischen Verbindungen dienen, und deren katalytischen Eigenschaften durch die Substitution der Amingruppe spezifisch auf Substrate eingestellt werden können.
PCT/EP2004/050439 2003-04-07 2004-04-05 Amin-substituierte diphenyldiphosphine und deren verwendung in metallkomplexen für asymmetrische synthesen WO2004089920A2 (de)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP04741445A EP1611114A2 (de) 2003-04-07 2004-04-05 Amin-substituierte diphenyldiphosphine und deren verwendung in metallkomplexen für asymmetrische synthesen
JP2006505522A JP2006523654A (ja) 2003-04-07 2004-04-05 アミン置換ジフェニルホスフィン
US10/552,066 US7589196B2 (en) 2003-04-07 2004-04-05 Amine-substituted biphenyldiphosphines
CA002521635A CA2521635A1 (en) 2003-04-07 2004-04-05 Amine-substituted diphenyldiphosphines and the use thereof in metal complexes for asymmetric syntheses

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH6242003 2003-04-07
CH0624/03 2003-04-07

Publications (3)

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WO2004089920A2 WO2004089920A2 (de) 2004-10-21
WO2004089920A3 true WO2004089920A3 (de) 2005-03-17
WO2004089920A8 WO2004089920A8 (de) 2005-05-26

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US (1) US7589196B2 (de)
EP (1) EP1611114A2 (de)
JP (1) JP2006523654A (de)
CN (1) CN1768046A (de)
CA (1) CA2521635A1 (de)
WO (1) WO2004089920A2 (de)

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Publication number Priority date Publication date Assignee Title
DE10328316A1 (de) 2003-06-23 2005-01-20 Grünenthal GmbH Verfahren zur Herstellung von Dimethyl-(3-aryl-buthyl)-aminverbindungen als pharmazeutische Wirkstoffe
DE102005052588A1 (de) * 2005-11-02 2007-05-10 Grünenthal GmbH Verfahren zur Herstellung substituierter Dimethyl-(3-aryl-butyl)-amin-Verbindungen mittels homogener Katalyse
TWI496762B (zh) 2006-07-24 2015-08-21 製備(1r,2r)-3-(3-二甲胺基-1-乙基-2-甲基-丙基)-酚之方法
FR3035880B1 (fr) * 2015-05-07 2017-06-02 Commissariat Energie Atomique Utilisation de nouveaux composes pour l'extraction selective de terres rares de solutions aqueuses comprenant de l'acide phosphorique et procede d'extraction associe

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4556740A (en) * 1982-08-27 1985-12-03 Hoffmann-La Roche Inc. Phosphorus compounds
EP0850945A1 (de) * 1996-12-26 1998-07-01 Takasago International Corporation Chirale Diphosphin-Verbindung, Zwischenprodukte zu ihrer Herstellung, Übergangsmetall-Komplexe davon und asymmetrischer Hydrierungskatalysator
EP1002801A1 (de) * 1998-11-19 2000-05-24 Solvias AG Chirale Diphenyldiphosphine und d-8 Metall-Komplexe davon

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4556740A (en) * 1982-08-27 1985-12-03 Hoffmann-La Roche Inc. Phosphorus compounds
EP0850945A1 (de) * 1996-12-26 1998-07-01 Takasago International Corporation Chirale Diphosphin-Verbindung, Zwischenprodukte zu ihrer Herstellung, Übergangsmetall-Komplexe davon und asymmetrischer Hydrierungskatalysator
EP1002801A1 (de) * 1998-11-19 2000-05-24 Solvias AG Chirale Diphenyldiphosphine und d-8 Metall-Komplexe davon

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SCHMID R ET AL: "NEW DEVELOPMENTS IN ENANTIOSELECTIVE HYDROGENATION", PURE & APPLIED CHEMISTRY, PERGAMON PRESS, OXFORD, GB, vol. 68, no. 1, 1996, pages 131 - 138, XP000884387, ISSN: 0033-4545 *

Also Published As

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EP1611114A2 (de) 2006-01-04
CA2521635A1 (en) 2004-10-21
CN1768046A (zh) 2006-05-03
US7589196B2 (en) 2009-09-15
WO2004089920A8 (de) 2005-05-26
US20060276643A1 (en) 2006-12-07
WO2004089920A2 (de) 2004-10-21
JP2006523654A (ja) 2006-10-19

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