GB1349895A - Catalytic asymmetric hydrogenation - Google Patents
Catalytic asymmetric hydrogenationInfo
- Publication number
- GB1349895A GB1349895A GB1349895DA GB1349895A GB 1349895 A GB1349895 A GB 1349895A GB 1349895D A GB1349895D A GB 1349895DA GB 1349895 A GB1349895 A GB 1349895A
- Authority
- GB
- United Kingdom
- Prior art keywords
- rhodium
- phosphine
- alkoxy
- arsine
- solution
- 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
Links
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 title 1
- 230000003197 catalytic effect Effects 0.000 title 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 3
- 229910052703 rhodium Inorganic materials 0.000 abstract 3
- 239000010948 rhodium Substances 0.000 abstract 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 150000002736 metal compounds Chemical class 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- WGHMKSPHCLPBTN-UHFFFAOYSA-N (2-methoxyphenyl)methyl-methyl-phenylphosphane Chemical compound COC1=CC=CC=C1CP(C)C1=CC=CC=C1 WGHMKSPHCLPBTN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 229910052785 arsenic Inorganic materials 0.000 abstract 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- ZMKOZQRDFHXOIH-UHFFFAOYSA-N cyclohexyl-[(2-methoxyphenyl)methyl]-methylphosphane Chemical compound COC1=CC=CC=C1CP(C)C1CCCCC1 ZMKOZQRDFHXOIH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229910052741 iridium Inorganic materials 0.000 abstract 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052762 osmium Inorganic materials 0.000 abstract 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003003 phosphines Chemical class 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 125000005936 piperidyl group Chemical group 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 150000003284 rhodium compounds Chemical class 0.000 abstract 1
- YWFDDXXMOPZFFM-UHFFFAOYSA-H rhodium(3+);trisulfate Chemical compound [Rh+3].[Rh+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YWFDDXXMOPZFFM-UHFFFAOYSA-H 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- WMUVAMXULTVKIW-UHFFFAOYSA-K tribromorhodium;hydrate Chemical compound O.Br[Rh](Br)Br WMUVAMXULTVKIW-UHFFFAOYSA-K 0.000 abstract 1
- HSSMNYDDDSNUKH-UHFFFAOYSA-K trichlororhodium;hydrate Chemical compound O.Cl[Rh](Cl)Cl HSSMNYDDDSNUKH-UHFFFAOYSA-K 0.000 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl 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
-
- 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
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/72—Aliphatic compounds
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F04—POSITIVE - DISPLACEMENT MACHINES FOR LIQUIDS; PUMPS FOR LIQUIDS OR ELASTIC FLUIDS
- F04C—ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT MACHINES FOR LIQUIDS; ROTARY-PISTON, OR OSCILLATING-PISTON, POSITIVE-DISPLACEMENT PUMPS
- F04C15/00—Component parts, details or accessories of machines, pumps or pumping installations, not provided for in groups F04C2/00 - F04C14/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
1349895 Hydrogenation catalysts MONSANTO CO 26 May 1971 17256/71 Heading B1E [Also in Division C2] A catalyst comprises a solution of a metal compound, the metal being rhodium, iridium, ruthenium, osmium, palladium or platinum, and at least one equivalent of an optically active phosphine or arsine per mole of metal in the solution. The terms "phosphine" and "arsine" as used herein mean PH 3 or AsH 3 or a compound derived by replacement of one or more hydrogen atoms in PH 3 or AsH 3 . The metal compound may be rhodium trichloride hydrate, rhodium tribromide hydrate, rhodium sulphate or a rhodium complex with an olefin. An active form of metallic rhodium which readily gives a rhodium compound in solution may also be used. The phosphine or arsine may have the formula AR<SP>5</SP>R<SP>6</SP>R<SP>7</SP> where A is phosphorus or arsenic, and R<SP>5</SP>, R<SP>6</SP> and R<SP>7</SP> are hydrogen; C 1-12 alkyl or alkoxy; alkyl substituted by one or more of NH 2 , COOH, carbonyl, aryl, NO 2 or C 1-4 alkoxy; aryl; aryloxy; phenyl substituted by one or more of alkoxy, alkyl, OH, aryloxy, NH 2 or NO 2 and the number of substituents being less than 3; cycloalkyl having at least 3C; substituted cycloalkyl; pyrrolyl; thienyl; furyl; pyridyl; piperidyl or 3-cholesteryl. Preferred phosphines are methylphenyl-o-anisyl phosphine and methyl cyclohexyl-o-anisyl phosphine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1725671 | 1971-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1349895A true GB1349895A (en) | 1974-04-10 |
Family
ID=10092005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1349895D Expired GB1349895A (en) | 1971-05-26 | 1971-05-26 | Catalytic asymmetric hydrogenation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1349895A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2376838A1 (en) * | 1977-01-07 | 1978-08-04 | American Cyanamid Co | Alpha-acylamino-crotonic and butyric acid derivs. - intermediates for direct synthesis of D-2-amino-butanol which is a precursor for ethambutol |
| GB2224277A (en) * | 1988-10-27 | 1990-05-02 | Occidental Chem Co | Chiral 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and l-phenylalanine derivatives |
-
1971
- 1971-05-26 GB GB1349895D patent/GB1349895A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2376838A1 (en) * | 1977-01-07 | 1978-08-04 | American Cyanamid Co | Alpha-acylamino-crotonic and butyric acid derivs. - intermediates for direct synthesis of D-2-amino-butanol which is a precursor for ethambutol |
| GB2224277A (en) * | 1988-10-27 | 1990-05-02 | Occidental Chem Co | Chiral 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and l-phenylalanine derivatives |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |