US20080281106A1 - Process for the Production of Asymmetric Transformation Catalysts - Google Patents

Process for the Production of Asymmetric Transformation Catalysts Download PDF

Info

Publication number
US20080281106A1
US20080281106A1 US10/586,204 US58620405A US2008281106A1 US 20080281106 A1 US20080281106 A1 US 20080281106A1 US 58620405 A US58620405 A US 58620405A US 2008281106 A1 US2008281106 A1 US 2008281106A1
Authority
US
United States
Prior art keywords
substituted
unsubstituted
group
chain alkyl
mmol
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.)
Abandoned
Application number
US10/586,204
Other languages
English (en)
Inventor
Wei-Ping Chen
John Whittall
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.)
Solvias AG
Original Assignee
Phoenix Chemicals Ltd
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 Phoenix Chemicals Ltd filed Critical Phoenix Chemicals Ltd
Assigned to PHOENIX CHEMICALS LIMITED reassignment PHOENIX CHEMICALS LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHEN, WEI-PING, WHITTALL, JOHN
Publication of US20080281106A1 publication Critical patent/US20080281106A1/en
Assigned to SOLVIAS AG reassignment SOLVIAS AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PHOENIX CHEMICALS LIMITED
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • B01J31/188—Amide 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
    • B01J31/189—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 containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
    • 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
    • B01J31/1895—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 arsenic or antimony
    • 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
    • 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
    • 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
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached 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
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
    • B01J31/2457—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings, e.g. Xantphos
    • 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
    • B01J31/2495—Ligands comprising a phosphine-P atom and one or more further complexing phosphorus atoms covered by groups B01J31/1845 - B01J31/1885, e.g. phosphine/phosphinate or phospholyl/phosphonate ligands
    • 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
    • C07F17/00—Metallocenes
    • 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
    • C07F17/00—Metallocenes
    • C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
    • 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
    • C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; 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
    • 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
    • B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • 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
    • 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
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron
    • 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
    • B01J2531/84—Metals of the iron group
    • B01J2531/847—Nickel

Definitions

  • the chiral ligand obtained by the process of the invention is a metallocene ligand
  • processes for producing ferrocene based ligands are preferred, but other suitable metals may be used in the metallocene ligands obtained by the process of the invention, and hence reference is made herein to metallocenes generally.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Led Devices (AREA)
  • Led Device Packages (AREA)
  • Control Of Eletrric Generators (AREA)
US10/586,204 2004-01-14 2005-01-14 Process for the Production of Asymmetric Transformation Catalysts Abandoned US20080281106A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB0400720.9A GB0400720D0 (en) 2004-01-14 2004-01-14 Novel ferrocene-based phosphorus chiral phosphines
GB0400720.9 2004-01-14
PCT/GB2005/000125 WO2005068478A1 (en) 2004-01-14 2005-01-14 Process for the production of asymmetric transformation catalysts

Publications (1)

Publication Number Publication Date
US20080281106A1 true US20080281106A1 (en) 2008-11-13

Family

ID=31726125

Family Applications (2)

Application Number Title Priority Date Filing Date
US10/586,204 Abandoned US20080281106A1 (en) 2004-01-14 2005-01-14 Process for the Production of Asymmetric Transformation Catalysts
US10/586,287 Expired - Fee Related US7994355B2 (en) 2004-01-14 2005-01-14 Metallocene-based chiral phosphine or arsine ligands

Family Applications After (1)

Application Number Title Priority Date Filing Date
US10/586,287 Expired - Fee Related US7994355B2 (en) 2004-01-14 2005-01-14 Metallocene-based chiral phosphine or arsine ligands

Country Status (11)

Country Link
US (2) US20080281106A1 (enExample)
EP (2) EP1725570B1 (enExample)
JP (2) JP2007517849A (enExample)
CN (2) CN1914218A (enExample)
AT (2) ATE404573T1 (enExample)
AU (2) AU2005205229B2 (enExample)
CA (2) CA2553607A1 (enExample)
DE (2) DE602005008917D1 (enExample)
ES (2) ES2323717T3 (enExample)
GB (4) GB0400720D0 (enExample)
WO (2) WO2005068478A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090137824A1 (en) * 2005-01-14 2009-05-28 Phoenix Chemicals Ltd Metallocene-based phosphorus chiral phosphines

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0400720D0 (en) * 2004-01-14 2004-02-18 Stylacats Ltd Novel ferrocene-based phosphorus chiral phosphines
DE602005003572T2 (de) * 2004-05-07 2008-04-17 Umicore Ag & Co. Kg Ferrocenylliganden für homogene, enantioselektive hydrierungskatalysatoren
US6906212B1 (en) * 2004-06-25 2005-06-14 Eastman Chemical Company Phosphine-phosphoramidite compounds
US6906213B1 (en) * 2004-06-25 2005-06-14 Eastman Chemical Company Preparation of aminophosphines
US20060135804A1 (en) * 2004-12-21 2006-06-22 Boaz Neil W Tetradentate ligands and metal complexes thereof for asymmetric catalysis
GB0500700D0 (en) * 2005-01-14 2005-02-23 Stylacats Ltd Process for the manufacture of 2-alkyl-3-phenylpropionic acids and alcohols
US8106227B2 (en) 2006-04-12 2012-01-31 Solviasag Ferrocenediphosphines
JP5209611B2 (ja) * 2006-05-23 2013-06-12 ソルヴィーアス アクチェンゲゼルシャフト 不斉付加反応、特に水素化における遷移金属触媒に使用されるキラルリガンド
JP5232989B2 (ja) * 2006-07-18 2013-07-10 国立大学法人豊橋技術科学大学 光学活性２，６−ビスアミノメチルピリジン誘導体とその製造方法およびその使用
JP5493346B2 (ja) * 2008-12-11 2014-05-14 東ソー株式会社 フェロセン誘導体およびその用途
PL2519100T3 (pl) 2009-12-29 2017-09-29 Mapi Pharma Limited Związki pośrednie i sposoby wytwarzania tapentadolu i pokrewnych związków
CN102775418B (zh) * 2012-06-11 2014-12-24 中国人民解放军第四军医大学 新型手性季铵盐相转移催化剂的合成及应用
CN104592313B (zh) * 2014-12-30 2017-08-25 陕西师范大学 基于二茂铁的双功能氢键有机催化剂及其制备方法和应用
CN104861001B (zh) * 2015-06-11 2017-08-04 河南省科学院化学研究所有限公司 一种二茂铁双膦配体的制备方法
EP3121179B1 (de) * 2015-07-23 2018-10-17 Evonik Degussa GmbH Ferrocenbasierte verbindungen und darauf basierende palladium-katalysatoren für die alkoxycarbonylierung ethylenisch ungesättigter verbindungen
ES2732998T3 (es) * 2016-07-19 2019-11-27 Evonik Operations Gmbh Ligandos 1,1'-bis(fosfino)ferroceno para la alcoxicarbonilación
CN109078653A (zh) * 2018-10-08 2018-12-25 浙江工业大学上虞研究院有限公司 手性二茂铁磷酸催化剂及其在不对称Friedel-Crafts反应中的应用
CN112824422B (zh) * 2019-11-21 2023-01-13 中国科学院大连化学物理研究所 一种手性二茂铁-吲哚双膦配体及其制备方法和其应用
CN114560893B (zh) * 2022-03-16 2024-02-06 中国科学院上海有机化学研究所 平面手性茂金属化合物、其合成方法及应用
CN116178455B (zh) * 2023-04-26 2023-08-18 江苏欣诺科催化剂股份有限公司 一种二茂铁类手性膦配体的制备方法

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5451684A (en) * 1993-05-14 1995-09-19 Lonza Ltd. Asymmetric hydrogenation of furoimidazole derivatives
US5466844A (en) * 1993-02-26 1995-11-14 Ciba-Geigy Corporation Ferrocene diphosphines as ligands for homogeneous catalysts
US5583241A (en) * 1993-10-01 1996-12-10 Ciba-Geigy Corporation Fluoroalkyl-substituted ferrocenyl diphosphines as ligands for homogeneous catalysts
US6194593B1 (en) * 2000-01-28 2001-02-27 Nippon Chemical Industrial Co., Ltd. 1, 2-bis(dialkylphosphino) benzene derivates having optical activites, process for producing same, and rhodium metal complexes containing same as ligands
US6258979B1 (en) * 1999-11-22 2001-07-10 Henri Kagan Chiral ferrocene phosphines active in asymmetric catalysis
US20020065417A1 (en) * 2000-09-29 2002-05-30 Boaz Neil Warren Phosphino-aminophosphines
US20050240007A1 (en) * 2002-04-30 2005-10-27 Paul Knochel Ferrocenyl ligands and method for the production of such ligands
US7994355B2 (en) * 2004-01-14 2011-08-09 Solvias Ag Metallocene-based chiral phosphine or arsine ligands

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU221611B (hu) * 1995-04-11 2002-11-28 Novartis Ag. Dihalogénezett ferrocének és előállítási eljárásaik
ES2183036T3 (es) 1996-04-25 2003-03-16 Hoechst Ag 2,2' - disustituidos-ferrocenos 2,2`-disustituidos y 1-fosfino-ferrocenos 1`,2-disustituidos, procedimiento para su preparacion, su utilizacion, asi como complejos de metales de transicion que los contienen,.
BR9712273A (pt) * 1996-10-07 1999-08-31 Novartis Ag Ferrocelinas quirais
EP0967015B1 (de) * 1998-06-19 2005-01-12 Degussa AG Verwendung von Ferrocenylliganden zur katalytischen enantioselektiven Hydrierung
DE19840279A1 (de) 1998-09-04 2000-03-09 Studiengesellschaft Kohle Mbh Neue chirale Diphosphonite auf Ferrocenbasis für die asymmetrische Katalyse
DE19952348A1 (de) * 1998-12-19 2000-06-21 Degussa Liganden und Komplexe zur enantioselektiven Hydrierung
CA2400183A1 (en) * 2000-02-10 2001-08-16 The Penn State Research Foundation Chiral ferrocene phosphines and their use in asymmetric catalytic reactions
CA2412910C (en) 2000-07-03 2010-11-16 Solvias Ag Ferrocenyl diphosphines and their use
CA2458430A1 (en) * 2001-10-05 2003-04-17 Solvias Ag Ligands for asymmetric reactions
DE10211250A1 (de) * 2002-03-13 2003-10-23 Degussa Ferrocenylliganden und ihre Verwendung in der Katalyse
US20080076937A1 (en) * 2004-07-05 2008-03-27 Benoit Pugin Tetradentate Ferrocene Ligands And Their Use

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5466844A (en) * 1993-02-26 1995-11-14 Ciba-Geigy Corporation Ferrocene diphosphines as ligands for homogeneous catalysts
US5451684A (en) * 1993-05-14 1995-09-19 Lonza Ltd. Asymmetric hydrogenation of furoimidazole derivatives
US5583241A (en) * 1993-10-01 1996-12-10 Ciba-Geigy Corporation Fluoroalkyl-substituted ferrocenyl diphosphines as ligands for homogeneous catalysts
US6258979B1 (en) * 1999-11-22 2001-07-10 Henri Kagan Chiral ferrocene phosphines active in asymmetric catalysis
US6194593B1 (en) * 2000-01-28 2001-02-27 Nippon Chemical Industrial Co., Ltd. 1, 2-bis(dialkylphosphino) benzene derivates having optical activites, process for producing same, and rhodium metal complexes containing same as ligands
US20020065417A1 (en) * 2000-09-29 2002-05-30 Boaz Neil Warren Phosphino-aminophosphines
US20050240007A1 (en) * 2002-04-30 2005-10-27 Paul Knochel Ferrocenyl ligands and method for the production of such ligands
US7994355B2 (en) * 2004-01-14 2011-08-09 Solvias Ag Metallocene-based chiral phosphine or arsine ligands

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090137824A1 (en) * 2005-01-14 2009-05-28 Phoenix Chemicals Ltd Metallocene-based phosphorus chiral phosphines
US7906669B2 (en) * 2005-01-14 2011-03-15 Solvias Ag Metallocene-based phosphorus chiral phosphines

Also Published As

Publication number Publication date
EP1709054B1 (en) 2009-03-04
GB2410950B (en) 2009-05-20
CN1914217A (zh) 2007-02-14
CA2553607A1 (en) 2005-07-28
DE602005013062D1 (de) 2009-04-16
GB0400720D0 (en) 2004-02-18
EP1725570A1 (en) 2006-11-29
ATE404573T1 (de) 2008-08-15
GB2410950A (en) 2005-08-17
JP2007517850A (ja) 2007-07-05
DE602005008917D1 (de) 2008-09-25
ATE424404T1 (de) 2009-03-15
JP2007517849A (ja) 2007-07-05
GB0905212D0 (en) 2009-05-13
CA2553608A1 (en) 2005-07-28
ES2313282T3 (es) 2009-03-01
AU2005205224B2 (en) 2009-04-23
GB2410951B (en) 2009-07-22
WO2005068477A1 (en) 2005-07-28
WO2005068478A1 (en) 2005-07-28
AU2005205224A1 (en) 2005-07-28
US7994355B2 (en) 2011-08-09
GB0500704D0 (en) 2005-02-23
EP1709054A1 (en) 2006-10-11
GB0500701D0 (en) 2005-02-23
GB2410951A (en) 2005-08-17
EP1725570B1 (en) 2008-08-13
CN1914218A (zh) 2007-02-14
AU2005205229A1 (en) 2005-07-28
AU2005205229B2 (en) 2010-03-04
ES2323717T3 (es) 2009-07-23
US20070161762A1 (en) 2007-07-12

Similar Documents

Publication Publication Date Title
US20080281106A1 (en) Process for the Production of Asymmetric Transformation Catalysts
Weber Phosphorus heterocycles: From laboratory curiosities to ligands in highly efficient catalysts
Atkinson et al. The syntheses and catalytic applications of unsymmetrical ferrocene ligands
Yang et al. Asymmetric catalytic carbon–carbon coupling reactions via C–H bond activation
US7109346B2 (en) N-phenyl-pyrrol bisphosphane compounds and the metal complexes of the same
EP0938488B1 (en) Phosphine ligands
AU2008318239B2 (en) Cationic transition metal catalysts
A. Stepanova et al. Synthesis of aminophosphines and their applications in catalysis
JPH11189600A (ja) ルテニウム錯体とこれを触媒とするアルコール化合物 の製造方法
EP1276745B1 (en) Ruthenium-diphosphine complexes and their use as catalysts
EP0667350A1 (en) Water-soluble phosphine-derivatives
Delacroix et al. Transition-metal-containing chiral bidentate ligands for enantioselective catalysis: non-metallocene architectural units come of age
JPH09249677A (ja) キラルなルテニウム錯体、その製造方法、及びプロキラルなケトンの鏡像選択的なトランスファー水素添加の方法
CA2524902C (en) Substituted ferrocenyldiphosphines as ligands for homogeneous hydrogenation catalysts
Godard et al. Systematic study of the asymmetric methoxycarbonylation of styrene catalyzed by palladium systems containing chiral ferrocenyl diphosphine ligands
JP2004502700A (ja) フェロセニルジホスフィンおよびその使用
CA2410410A1 (en) Chiral ligands for asymmetric catalysis
US20020151735A1 (en) Ligands and their use
Anderson et al. Synthesis of planar chiral ferrocenyl 1, 3-diamines and 1, 3-amino ethers
CA2740500A1 (en) Method for preparing a metal catalyst
EP1844061B1 (en) Metallocene-based phosphorus chiral phosphines
Hofmann et al. NHCP ligands for catalysis
US5202472A (en) Asymmetric hydrogenation of aromatic-substituted olefins using organonickel catalyst
Gajewy et al. From Noble Metals to Fe‐, Co‐, and Ni‐based Catalysts: A Case Study of Asymmetric Reductions
Mauduit et al. Asymmetric Catalysis with Metal N-Heterocyclic Carbene Complexes

Legal Events

Date Code Title Description
AS Assignment

Owner name: PHOENIX CHEMICALS LIMITED, UNITED KINGDOM

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHEN, WEI-PING;WHITTALL, JOHN;REEL/FRAME:018299/0330;SIGNING DATES FROM 20060717 TO 20060719

AS Assignment

Owner name: SOLVIAS AG, SWITZERLAND

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:PHOENIX CHEMICALS LIMITED;REEL/FRAME:023453/0802

Effective date: 20090722

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION