AU2005205224B2 - Metallocene-based chiral phosphine or arsine ligands - Google Patents

Metallocene-based chiral phosphine or arsine ligands Download PDF

Info

Publication number
AU2005205224B2
AU2005205224B2 AU2005205224A AU2005205224A AU2005205224B2 AU 2005205224 B2 AU2005205224 B2 AU 2005205224B2 AU 2005205224 A AU2005205224 A AU 2005205224A AU 2005205224 A AU2005205224 A AU 2005205224A AU 2005205224 B2 AU2005205224 B2 AU 2005205224B2
Authority
AU
Australia
Prior art keywords
substituted
unsubstituted
sfe
mmol
chirality
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
AU2005205224A
Other languages
English (en)
Other versions
AU2005205224A1 (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
Solvias AG
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 Solvias AG filed Critical Solvias AG
Publication of AU2005205224A1 publication Critical patent/AU2005205224A1/en
Assigned to PHOENIX CHEMICALS LIMITED reassignment PHOENIX CHEMICALS LIMITED Alteration of Name(s) of Applicant(s)/Patentee(s) Assignors: STYLACATS LIMITED
Application granted granted Critical
Publication of AU2005205224B2 publication Critical patent/AU2005205224B2/en
Assigned to SOLVIAS AG reassignment SOLVIAS AG Request for Assignment Assignors: PHOENIX CHEMICALS LIMITED
Anticipated expiration legal-status Critical
Ceased 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

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)
AU2005205224A 2004-01-14 2005-01-14 Metallocene-based chiral phosphine or arsine ligands Ceased AU2005205224B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0400720.9 2004-01-14
GBGB0400720.9A GB0400720D0 (en) 2004-01-14 2004-01-14 Novel ferrocene-based phosphorus chiral phosphines
PCT/GB2005/000112 WO2005068477A1 (en) 2004-01-14 2005-01-14 Metallocene-based chiral phosphine or arsine ligands

Publications (2)

Publication Number Publication Date
AU2005205224A1 AU2005205224A1 (en) 2005-07-28
AU2005205224B2 true AU2005205224B2 (en) 2009-04-23

Family

ID=31726125

Family Applications (2)

Application Number Title Priority Date Filing Date
AU2005205229A Ceased AU2005205229B2 (en) 2004-01-14 2005-01-14 Process for the production of asymmetric transformation catalysts
AU2005205224A Ceased AU2005205224B2 (en) 2004-01-14 2005-01-14 Metallocene-based chiral phosphine or arsine ligands

Family Applications Before (1)

Application Number Title Priority Date Filing Date
AU2005205229A Ceased AU2005205229B2 (en) 2004-01-14 2005-01-14 Process for the production of asymmetric transformation catalysts

Country Status (11)

Country Link
US (2) US7994355B2 (enExample)
EP (2) EP1725570B1 (enExample)
JP (2) JP2007517850A (enExample)
CN (2) CN1914217A (enExample)
AT (2) ATE424404T1 (enExample)
AU (2) AU2005205229B2 (enExample)
CA (2) CA2553608A1 (enExample)
DE (2) DE602005008917D1 (enExample)
ES (2) ES2313282T3 (enExample)
GB (4) GB0400720D0 (enExample)
WO (2) WO2005068477A1 (enExample)

Families Citing this family (21)

* 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
WO2005108409A2 (en) * 2004-05-07 2005-11-17 Umicore Ag & Co. Kg Ferrocenyl ligands for homogeneous, enantioselective hydrogenation catalysts
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
GB0500702D0 (en) * 2005-01-14 2005-02-23 Stylacats Ltd Novel metallocene-based phosphorus chiral phosphines
GB0500700D0 (en) * 2005-01-14 2005-02-23 Stylacats Ltd Process for the manufacture of 2-alkyl-3-phenylpropionic acids and alcohols
CN101421285B (zh) * 2006-04-12 2013-02-06 索尔维亚斯股份公司 二茂铁二膦
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
BR112012016059A2 (pt) 2009-12-29 2015-09-01 Mapi Pharma Ltd "compostos intermediários e processos para a preparação de tapentadol e compostos relacionados".
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
US9725398B2 (en) * 2015-07-23 2017-08-08 Evonik Degussa Gmbh Benzene-based diphosphine ligands for alkoxycarbonylation
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

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG42938A1 (en) * 1993-02-26 1997-10-17 Ciba Geigy Ag Ferrocenc diphosphines as ligands for homogeneous catalysts
CA2122511A1 (en) * 1993-05-14 1994-11-15 John Mcgarrity Asymmetric hydrogenation of furoimidazole derivatives
DE59408655D1 (de) * 1993-10-01 1999-09-30 Novartis Ag Mit Fluoralkyl substituierte Ferrocenyldiphosphine als Liganden für homogene Katalysatoren
AU5499296A (en) * 1995-04-11 1996-10-30 Novartis Ag Dihalogenated ferrocenes and processes for the preparation hereof
ATE223925T1 (de) 1996-04-25 2002-09-15 Hoechst Ag 2,2'-disubstituierte 1,1'-diphosphino-ferrocene und 1',2-disubstituierte 1-phosphino-ferrocene, verfahren zu ihrer herstellung, ihre verwendung sowie sie enthaltende übergangsmetallkomplexe
CZ292412B6 (cs) 1996-10-07 2003-09-17 Syngenta Participations Ag Chirální ferocenylové sloučeniny, způsob jejich přípravy a jejich použití
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
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
AU2001236912A1 (en) * 2000-02-10 2001-08-20 The Penn State Research Foundation Chiral ferrocene phosphines and their use in asymmetric catalytic reactions
ATE312111T1 (de) * 2000-07-03 2005-12-15 Solvias Ag Ferrocenyl-diphosphane und ihre verwendung
US6590115B2 (en) * 2000-09-29 2003-07-08 Eastman Chemical Company Phosphino-aminophosphines
ES2316646T3 (es) * 2001-10-05 2009-04-16 Solvias Ag Ligandos para reacciones asimetricas.
DE10211250A1 (de) * 2002-03-13 2003-10-23 Degussa Ferrocenylliganden und ihre Verwendung in der Katalyse
DE10219490A1 (de) * 2002-04-30 2003-11-13 Degussa Ferrocenylliganden und ein Verfahren zur Herstellung solcher Liganden
GB0400720D0 (en) * 2004-01-14 2004-02-18 Stylacats Ltd Novel ferrocene-based phosphorus chiral phosphines
DE502005001692D1 (de) * 2004-07-05 2007-11-22 Solvias Ag 1,1'diphosphinoferrocene mit 2,2'-gebundenen achiralen oder chiralen resten

Also Published As

Publication number Publication date
ES2323717T3 (es) 2009-07-23
AU2005205224A1 (en) 2005-07-28
EP1709054A1 (en) 2006-10-11
AU2005205229A1 (en) 2005-07-28
CA2553607A1 (en) 2005-07-28
DE602005008917D1 (de) 2008-09-25
GB2410950A (en) 2005-08-17
JP2007517850A (ja) 2007-07-05
GB2410951B (en) 2009-07-22
GB2410951A (en) 2005-08-17
GB0400720D0 (en) 2004-02-18
US7994355B2 (en) 2011-08-09
CN1914218A (zh) 2007-02-14
EP1725570B1 (en) 2008-08-13
GB2410950B (en) 2009-05-20
AU2005205229B2 (en) 2010-03-04
US20080281106A1 (en) 2008-11-13
WO2005068477A1 (en) 2005-07-28
EP1725570A1 (en) 2006-11-29
EP1709054B1 (en) 2009-03-04
CN1914217A (zh) 2007-02-14
GB0500704D0 (en) 2005-02-23
ATE424404T1 (de) 2009-03-15
ES2313282T3 (es) 2009-03-01
ATE404573T1 (de) 2008-08-15
US20070161762A1 (en) 2007-07-12
GB0905212D0 (en) 2009-05-13
GB0500701D0 (en) 2005-02-23
JP2007517849A (ja) 2007-07-05
DE602005013062D1 (de) 2009-04-16
CA2553608A1 (en) 2005-07-28
WO2005068478A1 (en) 2005-07-28

Similar Documents

Publication Publication Date Title
AU2005205224B2 (en) Metallocene-based chiral phosphine or arsine ligands
Togni et al. A novel easily accessible chiral ferrocenyldiphosphine for highly enantioselective hydrogenation, allylic alkylation, and hydroboration reactions
US20040116713A1 (en) Novel n-phenyl-pyrrol bisphosphane compounds and the metal complexes of the same
CA2382779C (en) Chiral ligands, transition-metal complexes thereof and uses thereof in asymmetric reactions
A. Stepanova et al. Synthesis of aminophosphines and their applications in catalysis
CA2203749C (en) 2,2'-disubstituted 1,1'-diphosphino-ferrocenes and 1',2-disubstituted 1-phosphino-ferrocenes, processes for preparing them, their use, and transition metal complexes comprising them
WO2005058917A2 (en) New oxazoline ligands for asymmetric catalysis
CA2540473A1 (en) Process for preparing cationic rhodium complexes
US6727377B2 (en) Asymmetric catalysis based on chiral phospholanes and hydroxyl phospholanes
US20040072680A1 (en) Chiral phosphorus cyclic compounds for transition metal-catalyzed asymmetric reactions
CA2410410A1 (en) Chiral ligands for asymmetric catalysis
US20020151735A1 (en) Ligands and their use
CN114085251B (zh) 一类手性二茂铁-螺环骨架双膦配体及其制备方法
US20040249184A1 (en) Novel chiral ligands, transition metal complexes thereof, and the catalytic use of the same
CA2594893C (en) Metallocene-based chiral phosphines and arsines
Mauduit et al. Asymmetric Catalysis with Metal N-Heterocyclic Carbene Complexes
US6043398A (en) Chemical processes using aryl diphosphine containing catalysts
CA2309193A1 (en) Catalysts for asymmetric syntheses containing rigid chiral ligands
Pugin et al. Twinphos: A New Family of Chiral Ferrocene Tetra-Phosphine Ligands for Asymmetric Catalytic Transformations
Liu Asymmetric synthesis of chiral phosphines and arsines promoted by organometallic complexes
Meriça et al. Ak› n Baysala, Hamdi Temelc, d

Legal Events

Date Code Title Description
PC1 Assignment before grant (sect. 113)

Owner name: PHOENIX CHEMICALS LIMITED

Free format text: FORMER APPLICANT(S): STYLACATS LIMITED

FGA Letters patent sealed or granted (standard patent)
PC Assignment registered

Owner name: SOLVIAS AG

Free format text: FORMER OWNER WAS: PHOENIX CHEMICALS LIMITED

MK14 Patent ceased section 143(a) (annual fees not paid) or expired