DE60020775T8 - Stereospezifische Isomerierung von Allylaminen unter Verwendung von immobilisierten chiralen Phospho-Liganden - Google Patents
Stereospezifische Isomerierung von Allylaminen unter Verwendung von immobilisierten chiralen Phospho-Liganden Download PDFInfo
- Publication number
- DE60020775T8 DE60020775T8 DE60020775T DE60020775T DE60020775T8 DE 60020775 T8 DE60020775 T8 DE 60020775T8 DE 60020775 T DE60020775 T DE 60020775T DE 60020775 T DE60020775 T DE 60020775T DE 60020775 T8 DE60020775 T8 DE 60020775T8
- Authority
- DE
- Germany
- Prior art keywords
- ligands
- phospho
- stereospecific
- chiral
- allylic amines
- 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.)
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- 239000003446 ligand Substances 0.000 title abstract 3
- 238000006317 isomerization reaction Methods 0.000 title abstract 2
- 230000000707 stereoselective effect Effects 0.000 title abstract 2
- -1 allylic amines Chemical class 0.000 title 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 4
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- 150000005347 biaryls Chemical group 0.000 abstract 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229930003633 citronellal Natural products 0.000 abstract 1
- 235000000983 citronellal Nutrition 0.000 abstract 1
- 150000002081 enamines Chemical class 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 229910052741 iridium Inorganic materials 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 150000003003 phosphines Chemical class 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 239000011343 solid material Substances 0.000 abstract 1
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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
-
- 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
- B01J31/165—Polymer immobilised coordination complexes, e.g. organometallic complexes
- B01J31/1658—Polymer immobilised coordination complexes, e.g. organometallic complexes immobilised by covalent linkages, i.e. pendant complexes with optional linking groups, e.g. on Wang or Merrifield resins
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- 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
- C07F9/50—Organo-phosphines
- C07F9/5027—Polyphosphines
-
- 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
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/52—Isomerisation reactions
-
- 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
- B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
- B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
-
- 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
- B01J2531/821—Ruthenium
-
- 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
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH113199 | 1999-06-17 | ||
| CH991131 | 1999-06-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE60020775D1 DE60020775D1 (de) | 2005-07-21 |
| DE60020775T2 DE60020775T2 (de) | 2006-05-11 |
| DE60020775T8 true DE60020775T8 (de) | 2006-09-28 |
Family
ID=4203230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60020775T Active DE60020775T8 (de) | 1999-06-17 | 2000-05-26 | Stereospezifische Isomerierung von Allylaminen unter Verwendung von immobilisierten chiralen Phospho-Liganden |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6350910B1 (de) |
| EP (1) | EP1060793B1 (de) |
| JP (1) | JP2001011029A (de) |
| AT (1) | ATE297807T1 (de) |
| DE (1) | DE60020775T8 (de) |
| ES (1) | ES2243171T3 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE324943T1 (de) * | 1999-09-20 | 2006-06-15 | Penn State Res Found | Chirale phosphine, deren komplexe mit übergangsmetallen und deren verwendung in asymmetrischen synthesereaktionen |
| KR100825615B1 (ko) * | 2001-12-27 | 2008-04-25 | 삼성토탈 주식회사 | 카르보디이미드계열 리간드의 킬레이트 화합물 촉매를이용한 에틸렌 중합 및 공중합방법 |
| KR100830319B1 (ko) * | 2001-12-27 | 2008-05-16 | 삼성토탈 주식회사 | 카르보디이미드계열 리간드의 킬레이트 화합물 촉매를 이용한 에틸렌 중합 또는 공중합 방법 |
| CN100389877C (zh) * | 2006-03-30 | 2008-05-28 | 复旦大学 | 一种用于常压制备手性仲醇的负载催化剂及其制备方法 |
| CN103272646B (zh) * | 2013-05-29 | 2015-02-11 | 上海灏翔生物科技有限公司 | 用于制备L-薄荷醇中间体d-香茅醛的催化剂及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS584748A (ja) | 1981-06-30 | 1983-01-11 | Takasago Corp | エナミンまたはイミンの製造方法 |
| JPS6061587A (ja) | 1983-09-16 | 1985-04-09 | Takasago Corp | ロジウム−ホスフイン錯体 |
| JPS60199898A (ja) | 1984-03-22 | 1985-10-09 | Takasago Corp | ロジウム−ホスフイン錯体 |
| JPS6119203A (ja) | 1984-07-05 | 1986-01-28 | Murata Mfg Co Ltd | ストリツプライン共振装置 |
| JPS6127949A (ja) * | 1984-07-17 | 1986-02-07 | Takasago Corp | 光学活性なエナミンの製造法 |
| ATE82745T1 (de) * | 1986-08-21 | 1992-12-15 | Hoffmann La Roche | Verfahren zur herstellung von optisch aktiven enaminen oder von den entsprechenden aldehyden. |
| ATE128140T1 (de) | 1989-05-18 | 1995-10-15 | Hoffmann La Roche | Phosphorverbindungen. |
| DE4330730A1 (de) | 1993-09-10 | 1995-03-16 | Bayer Ag | Neue Bisphosphine für asymmetrische Hydrierkatalysatoren |
| AU1575495A (en) | 1994-02-02 | 1995-08-21 | Ciba-Geigy Ag | Hydrogenation catalyst, process for the preparation thereof and hydrogenation process |
| DE19630536C2 (de) * | 1996-07-29 | 1998-11-05 | Hoechst Ag | Katalysator und dessen Verwendung für die Herstellung von Aldehyden durch Hydroformylierung olefinischer Verbindungen |
| GB9619684D0 (en) * | 1996-09-20 | 1996-11-06 | Oxford Asymmetry Ltd | Phosphine ligands |
| DE69913412T2 (de) * | 1998-04-07 | 2004-09-16 | Firmenich S.A. | Stereospezifische Isomerisierung von Allylaminen unter Verwendung von Chiralen Phospho-Liganden |
-
2000
- 2000-05-26 AT AT00111333T patent/ATE297807T1/de not_active IP Right Cessation
- 2000-05-26 ES ES00111333T patent/ES2243171T3/es not_active Expired - Lifetime
- 2000-05-26 DE DE60020775T patent/DE60020775T8/de active Active
- 2000-05-26 EP EP00111333A patent/EP1060793B1/de not_active Expired - Lifetime
- 2000-06-07 US US09/588,687 patent/US6350910B1/en not_active Expired - Fee Related
- 2000-06-16 JP JP2000182162A patent/JP2001011029A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001011029A (ja) | 2001-01-16 |
| DE60020775D1 (de) | 2005-07-21 |
| EP1060793A1 (de) | 2000-12-20 |
| ATE297807T1 (de) | 2005-07-15 |
| ES2243171T3 (es) | 2005-12-01 |
| EP1060793B1 (de) | 2005-06-15 |
| US6350910B1 (en) | 2002-02-26 |
| DE60020775T2 (de) | 2006-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |