IL89325A - Optically active rhodium complexes of 3,4-bis (diarylphosphino) pyrrolidines and their use for the preparation of phosphinothricin by asymmetric hydrogenation. - Google Patents

Optically active rhodium complexes of 3,4-bis (diarylphosphino) pyrrolidines and their use for the preparation of phosphinothricin by asymmetric hydrogenation.

Info

Publication number: IL89325A
Authority: IL; Israel
Prior art keywords: formula; rhodium complex; denotes; rhodium; preparation
Prior art date: 1988-02-19

Application number

IL8932589A

Other languages

English (en)

Other versions

IL89325A0 (en

Original Assignee

Hoechst 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.)

1988-02-19

Filing date

1989-02-17

Publication date

1995-03-15

1989-02-17 Application filed by Hoechst Ag filed Critical Hoechst Ag

1989-09-10 Publication of IL89325A0 publication Critical patent/IL89325A0/xx

1995-03-15 Publication of IL89325A publication Critical patent/IL89325A/en

Links

238000002360 preparation method Methods 0.000 title claims description 12
150000003283 rhodium Chemical class 0.000 title claims description 6
IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 title claims description 4
238000009876 asymmetric hydrogenation reaction Methods 0.000 title description 4
150000003235 pyrrolidines Chemical class 0.000 title description 4
IAJOBQBIJHVGMQ-UHFFFAOYSA-N Phosphinothricin Natural products CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 title description 2
239000010948 rhodium Substances 0.000 claims description 42
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 31
229910052703 rhodium Inorganic materials 0.000 claims description 30
239000003054 catalyst Substances 0.000 claims description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 16
238000000034 method Methods 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
239000000047 product Substances 0.000 claims description 11
239000000758 substrate Substances 0.000 claims description 11
-1 tetrafluoroborate Chemical compound 0.000 claims description 10
239000004912 1,5-cyclooctadiene Substances 0.000 claims description 9
238000005984 hydrogenation reaction Methods 0.000 claims description 8
239000010695 polyglycol Substances 0.000 claims description 8
229920000151 polyglycol Polymers 0.000 claims description 7
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 5
125000005442 diisocyanate group Chemical group 0.000 claims description 5
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 5
VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000732 arylene group Chemical group 0.000 claims description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
230000003287 optical effect Effects 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
229920001223 polyethylene glycol Polymers 0.000 description 11
239000002202 Polyethylene glycol Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000012948 isocyanate Substances 0.000 description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
150000002513 isocyanates Chemical class 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
150000003254 radicals Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000004448 titration Methods 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
YMRKZKDKJJCIHH-VSGBNLITSA-N [(3r,4r)-4-diphenylphosphanylpyrrolidin-3-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P([C@H]1[C@@H](CNC1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 YMRKZKDKJJCIHH-VSGBNLITSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
AUXMWYRZQPIXCC-KNIFDHDWSA-N (2s)-2-amino-4-methylpentanoic acid;(2s)-2-aminopropanoic acid Chemical compound C[C@H](N)C(O)=O.CC(C)C[C@H](N)C(O)=O AUXMWYRZQPIXCC-KNIFDHDWSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical group Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
238000004679 31P NMR spectroscopy Methods 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
YODNAXUBSDNADY-QZTJIDSGSA-N C1(=C(C=CC=C1)P[C@@H]1CNC[C@H]1PC1=C(C=CC=C1)C)C Chemical compound C1(=C(C=CC=C1)P[C@@H]1CNC[C@H]1PC1=C(C=CC=C1)C)C YODNAXUBSDNADY-QZTJIDSGSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000005058 Isophorone diisocyanate Substances 0.000 description 1
DEFJQIDDEAULHB-IMJSIDKUSA-N L-alanyl-L-alanine Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(O)=O DEFJQIDDEAULHB-IMJSIDKUSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
108010056243 alanylalanine Proteins 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
239000004913 cyclooctene Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic 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
- 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
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
General Chemical & Material Sciences (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyethers (AREA)
Polyurethanes Or Polyureas (AREA)

IL8932589A 1988-02-19 1989-02-17 Optically active rhodium complexes of 3,4-bis (diarylphosphino) pyrrolidines and their use for the preparation of phosphinothricin by asymmetric hydrogenation. IL89325A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3805151		1988-02-19
DE3818435A DE3818435A1 (de)	1988-02-19	1988-05-31	Optisch aktive rhodiumkomplexe von 3,4-bis(diarylphosphino)-pyrrolidinen und ihre verwendung zur herstellung von phosphinothricin durch asymmetrische hydrierung

Publications (2)

Publication Number	Publication Date
IL89325A0 IL89325A0 (en)	1989-09-10
IL89325A true IL89325A (en)	1995-03-15

Family

ID=25865007

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL8932589A IL89325A (en)	1988-02-19	1989-02-17	Optically active rhodium complexes of 3,4-bis (diarylphosphino) pyrrolidines and their use for the preparation of phosphinothricin by asymmetric hydrogenation.

Country Status (8)

Country	Link
US (2)	US4923996A (da)
EP (1)	EP0329043B1 (da)
JP (1)	JPH024819A (da)
CA (1)	CA1337723C (da)
DE (2)	DE3818435A1 (da)
DK (1)	DK74789A (da)
ES (1)	ES2061747T3 (da)
IL (1)	IL89325A (da)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1338384A (fr) *	1962-07-03	1963-09-27	Acec	Procédé de fabrication au défilé de tubes avec ailettes latérales ou de produits similaires
US6191105B1 (en) *	1993-05-10	2001-02-20	Protein Delivery, Inc.	Hydrophilic and lipophilic balanced microemulsion formulations of free-form and/or conjugation-stabilized therapeutic agents such as insulin
ATE222932T1 (de) *	1995-02-24	2002-09-15	Novartis Erfind Verwalt Gmbh	An seitenketten von polymeren gebundene diphosphine und deren metall-komplexe
US5777062A (en) *	1996-02-23	1998-07-07	Novartis Corporation	Diphosphines bonded to side chains of polymers, and metal complexes thereof
FR2790477B1 (fr) *	1999-03-01	2001-05-25	Rhodia Chimie Sa	Polymere lineaire optiquement actif utilisable comme ligand dans la preparation de complexes metalliques destines a la catalyse asymetrique
WO2001004131A1 (en) *	1999-07-14	2001-01-18	Solvias Ag	Diphosphine ligands for metal complexes
DE10002976A1 (de) *	2000-01-24	2001-07-26	Degussa	Molekulargewichtsvergrößerte Liganden für asymmetrische homogen lösliche Hydrierkatalysatoren, Verfahren zu deren Herstellung und Verwendung
DE10002973A1 (de) *	2000-01-24	2001-07-26	Degussa	Polymere Diphosphinliganden für homogen lösliche Hydrierkatalysatoren, Verfahren zu deren Herstellung und Verwendung
US20050101813A1 (en) *	2003-09-08	2005-05-12	Degussa Ag,	Molecular weight-enlarged ligands for asymmetric, homogeneously soluble hydrogenation catalysts, process for the production thereof and use

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2717440C2 (de) *	1976-05-17	1984-04-05	Hoechst Ag, 6230 Frankfurt	Unkrautbekämpfung mit [(3-Amino-3-carboxy)-propyl-1]-methylphosphinsäure-Derivaten
US4265654A (en) *	1977-12-28	1981-05-05	Meiji Seika Kaisha Ltd.	Herbicidal compositions
DE3403194A1 (de) *	1984-01-31	1985-08-01	Degussa Ag, 6000 Frankfurt	Optisch aktive 3,4-bis-(diphenylphosphino)-pyrrolidine, diese als chirale liganden enthaltende rhodiumkomplexe und deren verwendung
DE3609818A1 (de) *	1986-03-22	1987-09-24	Hoechst Ag	Verfahren zur herstellung von l-phosphinothricin(derivaten) sowie ihrer alkylester

1988
- 1988-05-31 DE DE3818435A patent/DE3818435A1/de not_active Withdrawn
1989
- 1989-02-11 ES ES89102381T patent/ES2061747T3/es not_active Expired - Lifetime
- 1989-02-11 DE DE89102381T patent/DE58906606D1/de not_active Expired - Fee Related
- 1989-02-11 EP EP89102381A patent/EP0329043B1/de not_active Expired - Lifetime
- 1989-02-16 JP JP1035160A patent/JPH024819A/ja active Pending
- 1989-02-17 CA CA000591406A patent/CA1337723C/en not_active Expired - Fee Related
- 1989-02-17 US US07/312,030 patent/US4923996A/en not_active Expired - Fee Related
- 1989-02-17 IL IL8932589A patent/IL89325A/en not_active IP Right Cessation
- 1989-02-17 DK DK074789A patent/DK74789A/da not_active Application Discontinuation
1990
- 1990-01-17 US US07/466,217 patent/US5043474A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA1337723C (en)	1995-12-12
US5043474A (en)	1991-08-27
IL89325A0 (en)	1989-09-10
EP0329043A3 (en)	1990-11-22
DK74789A (da)	1989-08-20
EP0329043A2 (de)	1989-08-23
DK74789D0 (da)	1989-02-17
US4923996A (en)	1990-05-08
DE3818435A1 (de)	1989-08-31
JPH024819A (ja)	1990-01-09
DE58906606D1 (de)	1994-02-17
EP0329043B1 (de)	1994-01-05
ES2061747T3 (es)	1994-12-16

Legal Events

Date	Code	Title	Description
2000-01-31	RH	Patent void

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