DK169074B1 - Chirale rhodium-disphosphincomplexer, fremgangsmåde til fremstilling deraf samt anvendelse af complexerne - Google Patents

Chirale rhodium-disphosphincomplexer, fremgangsmåde til fremstilling deraf samt anvendelse af complexerne Download PDF

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Publication number
DK169074B1
DK169074B1 DK141585A DK141585A DK169074B1 DK 169074 B1 DK169074 B1 DK 169074B1 DK 141585 A DK141585 A DK 141585A DK 141585 A DK141585 A DK 141585A DK 169074 B1 DK169074 B1 DK 169074B1
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Prior art keywords
chiral
general formula
alkyl
rhodium
complexes
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DK141585A
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Danish (da)
English (en)
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DK141585A (da
DK141585D0 (da
Inventor
Emil Albin Broger
Yvo Crameri
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Hoffmann La Roche
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Publication of DK141585A publication Critical patent/DK141585A/da
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Publication of DK169074B1 publication Critical patent/DK169074B1/da

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073—Rhodium compounds
    • C07F15/008—Rhodium compounds without a metal-carbon linkage
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • 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
    • B01J31/2291—Olefins
    • 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
    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • 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
    • B01J2531/80—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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
    • 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
    • B01J31/1805—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 nitrogen
    • 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)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)
DK141585A 1984-04-19 1985-03-28 Chirale rhodium-disphosphincomplexer, fremgangsmåde til fremstilling deraf samt anvendelse af complexerne DK169074B1 (da)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH196784 1984-04-19
CH196784 1984-04-19
CH54785 1985-02-07
CH54785 1985-02-07

Publications (3)

Publication Number Publication Date
DK141585D0 DK141585D0 (da) 1985-03-28
DK141585A DK141585A (da) 1985-10-20
DK169074B1 true DK169074B1 (da) 1994-08-08

Family

ID=25684922

Family Applications (1)

Application Number Title Priority Date Filing Date
DK141585A DK169074B1 (da) 1984-04-19 1985-03-28 Chirale rhodium-disphosphincomplexer, fremgangsmåde til fremstilling deraf samt anvendelse af complexerne

Country Status (5)

Country Link
US (1) US4652657A (fr)
EP (1) EP0158875B1 (fr)
JP (1) JPH0713076B2 (fr)
DE (1) DE3574704D1 (fr)
DK (1) DK169074B1 (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE77383T1 (de) * 1985-10-18 1992-07-15 Hoffmann La Roche Chirale rhodium-diphosphinkomplexe fuer asymmetrische hydrierungen.
JP2816555B2 (ja) * 1988-03-07 1998-10-27 富士薬品工業株式会社 新規なホスフイノピロリジン化合物およびそれを用いる不斉合成法
US4870208A (en) * 1988-06-03 1989-09-26 Monsanto Company Asymmetric hydrogenolysis of epoxides
US5103043A (en) * 1989-03-03 1992-04-07 Shell Oil Company Carbonylation catalyst system
KR0148012B1 (ko) * 1989-03-03 1998-08-17 오노 알버어스 신규한 포스핀으로 구성되는 촉매시스템 및 이를 이용한 아세틸렌형 또는 올레핀형 불포화화합물의 카르보닐화방법
US5110955A (en) * 1989-04-14 1992-05-05 Hoffmann-La Roche Inc. Tocopherol synthesis: chromane cyclization and catalysis
DE4001019A1 (de) * 1990-01-16 1991-07-18 Degussa Verfahren zur asymmetrischen hydrierung von (alpha)-ketocarbonylverbindungen zu optisch aktiven (alpha)-hydroxycarbonylverbindungen
FR2666250A1 (fr) * 1990-09-05 1992-03-06 Rhone Poulenc Nutrition Animal Nouveaux catalyseurs, procede de preparation et leur utilisation.
US5374727A (en) * 1992-06-19 1994-12-20 Hoffmann-La Roche Inc. Asymmetric hydrogenation of dihydro-pyrido [1,2-a]indoles
FR2693190B1 (fr) * 1992-07-02 1994-09-23 Elf Aquitaine Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO.
DE19725796A1 (de) * 1997-06-18 1998-12-24 Basf Ag Herstellung optisch aktiver Phospholane, deren Metallkomplexe und Anwendung in der asymmetrischen Synthese
DE19725643A1 (de) * 1997-06-18 1998-12-24 Basf Ag Optisch aktive Diphosphinliganden
JP4674393B2 (ja) * 2000-06-21 2011-04-20 ダイキン工業株式会社 光学活性な含フッ素β−ヒドロキシエステルの製造方法
EP1765763A2 (fr) 2004-07-07 2007-03-28 Basf Aktiengesellschaft Procede de production d'esters monoalkyle-acide succinique-alkyle optiquement actifs
WO2006097314A1 (fr) * 2005-03-17 2006-09-21 Basf Aktiengesellschaft Procede pour produire des derives d'acide propionique 3-phenyle optiquement actifs et produits reactionnels en decoulant
EP2480664A1 (fr) 2009-09-25 2012-08-01 Basf Se Amidase et son utilisation pour la production d'esters d'acide 3-aminocarboxilique
CN104761518B (zh) * 2014-12-01 2017-05-24 青岛科技大学 一种离子液体条件下不对称氢化合成d‑泛内酯的方法
WO2019199540A1 (fr) * 2018-04-13 2019-10-17 Archer Daniels Midland Company Déshydratation et craquage de composés alpha-, bêta-dihydroxycarbonyle en acide lactique et autres produits

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1601121A (fr) * 1968-10-01 1970-08-10
GB1368431A (en) * 1970-07-22 1974-09-25 Johnson Matthey Co Ltd Rhodium complex and methods of preparing the complex
JPS5466672A (en) * 1977-11-04 1979-05-29 Fuji Yakuhin Kogyo Kk Novel unsymmetrical hydrogenated catalyst nnacyllmethylpyrrolidine bisphosphineerhodium complex compounds and manufacture
IL59647A (en) * 1980-03-14 1984-01-31 Yeda Res & Dev Organo-metallic catalytic system
US4343741A (en) * 1981-04-22 1982-08-10 Hoffmann-La Roche Inc. Chiral phosphines
CH651051A5 (en) * 1982-02-05 1985-08-30 Hoffmann La Roche Phosphorus compounds
US4539411A (en) * 1982-02-05 1985-09-03 Hoffmann-La Roche Inc. Rhodium complexes of chiral phosphines

Also Published As

Publication number Publication date
EP0158875B1 (fr) 1989-12-13
EP0158875A2 (fr) 1985-10-23
EP0158875A3 (en) 1986-10-08
DK141585A (da) 1985-10-20
JPS60243093A (ja) 1985-12-03
JPH0713076B2 (ja) 1995-02-15
DE3574704D1 (de) 1990-01-18
DK141585D0 (da) 1985-03-28
US4652657A (en) 1987-03-24

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