FR2521145B1 - Phosphines chirales, procedes pour leur preparation, produits intermediaires de leur preparation, complexes de rhodium de ces phosphines et utilisation de ces derniers dans des hydrogenations asymetriques - Google Patents

Phosphines chirales, procedes pour leur preparation, produits intermediaires de leur preparation, complexes de rhodium de ces phosphines et utilisation de ces derniers dans des hydrogenations asymetriques

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Publication number
FR2521145B1
FR2521145B1 FR8301684A FR8301684A FR2521145B1 FR 2521145 B1 FR2521145 B1 FR 2521145B1 FR 8301684 A FR8301684 A FR 8301684A FR 8301684 A FR8301684 A FR 8301684A FR 2521145 B1 FR2521145 B1 FR 2521145B1
Authority
FR
France
Prior art keywords
preparation
processes
same
intermediate products
rhodium complexes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
FR8301684A
Other languages
English (en)
Other versions
FR2521145A1 (fr
Inventor
Emil Albin Broger
Yvo Crameri
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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
Priority claimed from CH711/82A external-priority patent/CH651051A5/de
Priority claimed from CH7010/82A external-priority patent/CH653338A5/de
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of FR2521145A1 publication Critical patent/FR2521145A1/fr
Application granted granted Critical
Publication of FR2521145B1 publication Critical patent/FR2521145B1/fr
Expired legal-status Critical Current

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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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • 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
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered 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
    • 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
    • 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
    • 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
    • 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)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
FR8301684A 1982-02-05 1983-02-03 Phosphines chirales, procedes pour leur preparation, produits intermediaires de leur preparation, complexes de rhodium de ces phosphines et utilisation de ces derniers dans des hydrogenations asymetriques Expired FR2521145B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH711/82A CH651051A5 (en) 1982-02-05 1982-02-05 Phosphorus compounds
CH7010/82A CH653338A5 (en) 1982-12-02 1982-12-02 Phosphorus compounds

Publications (2)

Publication Number Publication Date
FR2521145A1 FR2521145A1 (fr) 1983-08-12
FR2521145B1 true FR2521145B1 (fr) 1986-09-12

Family

ID=25685452

Family Applications (1)

Application Number Title Priority Date Filing Date
FR8301684A Expired FR2521145B1 (fr) 1982-02-05 1983-02-03 Phosphines chirales, procedes pour leur preparation, produits intermediaires de leur preparation, complexes de rhodium de ces phosphines et utilisation de ces derniers dans des hydrogenations asymetriques

Country Status (7)

Country Link
US (2) US4539411A (fr)
AT (1) AT389312B (fr)
DE (1) DE3302697A1 (fr)
FR (1) FR2521145B1 (fr)
GB (1) GB2114134B (fr)
IT (1) IT1175910B (fr)
NL (1) NL8300354A (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3574704D1 (de) * 1984-04-19 1990-01-18 Hoffmann La Roche Chirale rhodium-diphosphinkomplexe fuer asymmetrische hydrierungen.
DE3446303A1 (de) * 1984-12-19 1986-06-19 Degussa Ag, 6000 Frankfurt Verfahren zur herstellung von optisch aktivem 1-benzyl-3,4-bis-(diphenylphosphino)-pyrrolidin
DE3685713D1 (de) * 1985-10-18 1992-07-23 Hoffmann La Roche Chirale rhodium-diphosphinkomplexe fuer asymmetrische hydrierungen.
FR2600330B1 (fr) * 1986-06-23 1988-12-16 Charbonnages Ste Chimique Procede d'hydrogenation asymetrique de composes carbonyles et composes obtenus
EP0251164B1 (fr) * 1986-06-25 1992-12-16 Kazuo Achiwa Composés chiraux de phosphinopyrrolidine et leur utilisation pour la synthèse asymétrique de composés optiquement actifs
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
US5036153A (en) * 1989-05-11 1991-07-30 Braish Tamim F Preparation of 2,5-diazabicyclo[2.2.1]heptanes and intermediates
US5286902A (en) * 1991-04-15 1994-02-15 Koch Industries, Inc. Process for preparation of 2-(6-methoxy-2-naphthyl)propionic acid and intermediates therefor utilizing 2,6-diisopropylnaphthalene
AU5191898A (en) * 1996-11-29 1998-06-22 Fuji Yakuhin Kogyo Kabushiki Kaisha Novel phosphinopyrrolidine compounds and process for producing the same
DE19831137A1 (de) * 1998-07-11 2000-01-13 Studiengesellschaft Kohle Mbh Asymmetrische katalytische Hydrierung von Olefinen
US6589978B2 (en) * 2000-06-30 2003-07-08 Hoffman-La Roche Inc. 1-sulfonyl pyrrolidine derivatives
TW201109335A (en) 2009-08-04 2011-03-16 Takeda Pharmaceutical Heterocyclic compounds

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4119652A (en) * 1974-08-29 1978-10-10 Monsanto Company Catalytic asymmetric hydrogenation
JPS53105421A (en) * 1977-02-28 1978-09-13 Sagami Chem Res Center Preparation of optical active alpha-hydroxycarboxylic acid esters acid esters
US4168381A (en) * 1977-06-14 1979-09-18 American Cyanamid Company Enhancement of enantioselectivity by iodide salts of Rh(I) complexes in the reduction of prochiral imidazolinones
JPS54160365A (en) * 1978-06-04 1979-12-19 Fuji Yakuhin Kogyo Kk Phosphine contained pyrrolidine compound and its manufacture
JPS5639097A (en) * 1979-09-07 1981-04-14 Sagami Chem Res Center Optically active n-carbamoylpyrrolidinodiphosphine ligand and its preparation
JPS57145891A (en) * 1981-03-05 1982-09-09 Sagami Chem Res Center Optically active diphosphine ligand
US4424312A (en) * 1981-03-16 1984-01-03 Polymer Sciences Corporation Preparation of amino acids in high optical yield via catalytic hydrogenation
US4343741A (en) * 1981-04-22 1982-08-10 Hoffmann-La Roche Inc. Chiral phosphines

Also Published As

Publication number Publication date
GB8303161D0 (en) 1983-03-09
NL8300354A (nl) 1983-09-01
FR2521145A1 (fr) 1983-08-12
GB2114134A (en) 1983-08-17
AT389312B (de) 1989-11-27
ATA39383A (de) 1989-04-15
IT1175910B (it) 1987-08-12
US4539411A (en) 1985-09-03
US4620013A (en) 1986-10-28
GB2114134B (en) 1985-10-09
DE3302697A1 (de) 1983-08-18
IT8319195A0 (it) 1983-01-20

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