JP4397524B2 - 環式ホスフィンの調製法 - Google Patents
環式ホスフィンの調製法 Download PDFInfo
- Publication number
- JP4397524B2 JP4397524B2 JP2000520453A JP2000520453A JP4397524B2 JP 4397524 B2 JP4397524 B2 JP 4397524B2 JP 2000520453 A JP2000520453 A JP 2000520453A JP 2000520453 A JP2000520453 A JP 2000520453A JP 4397524 B2 JP4397524 B2 JP 4397524B2
- Authority
- JP
- Japan
- Prior art keywords
- phosphine
- formula
- alkyl
- cyclic
- aryl
- 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 - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- -1 cyclic phosphines Chemical class 0.000 title claims description 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 46
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 18
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 18
- 239000002168 alkylating agent Substances 0.000 claims abstract description 17
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 10
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 230000029936 alkylation Effects 0.000 claims abstract description 3
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 32
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- DKFDVEXWZZOMGS-UHFFFAOYSA-N (2-phosphanylphenyl)phosphane Chemical compound PC1=CC=CC=C1P DKFDVEXWZZOMGS-UHFFFAOYSA-N 0.000 claims description 5
- FWFZRPMNAAFGBA-UHFFFAOYSA-N 2-phosphanylethylphosphane Chemical compound PCCP FWFZRPMNAAFGBA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims 2
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 230000002452 interceptive effect Effects 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 4
- 238000006073 displacement reaction Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
- 239000003446 ligand Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- RVZJVYCTFGOEHX-UHFFFAOYSA-N phosphetane Chemical compound C1CPC1 RVZJVYCTFGOEHX-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 150000003003 phosphines Chemical class 0.000 description 4
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- LLXIGVGFZQLRES-VXGBXAGGSA-N (2r,4r)-2,4-diethyl-1-phenylphosphetane Chemical compound CC[C@@H]1C[C@@H](CC)P1C1=CC=CC=C1 LLXIGVGFZQLRES-VXGBXAGGSA-N 0.000 description 2
- AJNZWRKTWQLAJK-KLHDSHLOSA-N (2r,5r)-1-[2-[(2r,5r)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane Chemical compound C[C@@H]1CC[C@@H](C)P1C1=CC=CC=C1P1[C@H](C)CC[C@H]1C AJNZWRKTWQLAJK-KLHDSHLOSA-N 0.000 description 2
- AJNZWRKTWQLAJK-VGWMRTNUSA-N (2s,5s)-1-[2-[(2s,5s)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane Chemical compound C[C@H]1CC[C@H](C)P1C1=CC=CC=C1P1[C@@H](C)CC[C@@H]1C AJNZWRKTWQLAJK-VGWMRTNUSA-N 0.000 description 2
- 150000000190 1,4-diols Chemical class 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007068 beta-elimination reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- FVWCDFMLOYFXCE-UHFFFAOYSA-N naphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P)=CC=CC2=C1 FVWCDFMLOYFXCE-UHFFFAOYSA-N 0.000 description 2
- 125000001979 organolithium group Chemical group 0.000 description 2
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000000185 1,3-diols Chemical class 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 238000003800 Staudinger reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 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 description 1
- 230000002210 biocatalytic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Inorganic materials [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical compound [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 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
- 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
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
- C07F9/5072—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure P-H
-
- 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
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- 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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9723583.2A GB9723583D0 (en) | 1997-11-07 | 1997-11-07 | Process for cyclic phosphines |
| US6867597P | 1997-12-24 | 1997-12-24 | |
| US9723583.2 | 1997-12-24 | ||
| US60/068,675 | 1997-12-24 | ||
| PCT/GB1998/003321 WO1999024444A1 (en) | 1997-11-07 | 1998-11-05 | Process for preparing cyclic phosphines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001522855A JP2001522855A (ja) | 2001-11-20 |
| JP2001522855A5 JP2001522855A5 (cg-RX-API-DMAC7.html) | 2006-01-05 |
| JP4397524B2 true JP4397524B2 (ja) | 2010-01-13 |
Family
ID=26312567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000520453A Expired - Fee Related JP4397524B2 (ja) | 1997-11-07 | 1998-11-05 | 環式ホスフィンの調製法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6545183B1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1028967B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4397524B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE206128T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU1041099A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2307192A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69801841T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2162473T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO1999024444A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9814170D0 (en) | 1998-06-30 | 1998-08-26 | Chirotech Technology Ltd | The preparation of arylphosphines |
| WO2000000498A1 (en) * | 1998-06-30 | 2000-01-06 | Chirotech Technology Limited | The preparation of arylphosphines |
| GB9823716D0 (en) | 1998-10-29 | 1998-12-23 | Isis Innovation | Diphosphines |
| CA2347146A1 (en) * | 1998-11-05 | 2000-05-18 | Chirotech Technology Limited | Chiral ligands for asymmetric catalysis |
| JP4037756B2 (ja) * | 2000-12-13 | 2008-01-23 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | Ｐ−キラルビスホスホランリガンド、それらの遷移金属錯体 |
| DE10106348A1 (de) * | 2001-02-09 | 2002-08-14 | Basf Ag | Als Katalysator oder zur Herstellung eines Katalysatorsystems geeignete Verbindung |
| EP1451133B1 (en) * | 2001-11-09 | 2017-10-25 | The Penn State Research Foundation | P-chiral phospholanes and phosphocyclic compounds and their use in asymmetric catalytic reactions |
| US7169953B2 (en) * | 2001-11-09 | 2007-01-30 | The Penn State Research Foundation | P-chiral phospholanes and phosphocyclic compounds and their use in asymmetric catalytic reactions |
| ITMI20020415A1 (it) | 2002-03-01 | 2003-09-01 | Chemi Spa | Catalizzatori metallici per reazione chemo- regio- stereo-selettive erelativi precursori |
| WO2005010013A1 (ja) * | 2003-07-28 | 2005-02-03 | Nippon Chemical Industrial Co., Ltd. | 新規光学活性リンキラルジホスフェタン化合物、該化合物の中間体、及び該化合物を配位子とする遷移金属錯体 |
| DE10353831A1 (de) * | 2003-11-18 | 2005-06-23 | Degussa Ag | Verfahren zur Herstellung von Bisphospholanliganden |
| WO2006020639A2 (en) * | 2004-08-12 | 2006-02-23 | Sigma-Aldrich Co. | Stabilized borane-tetrahydrofuran complex |
| JP2008538585A (ja) * | 2005-04-22 | 2008-10-30 | ダウ グローバル テクノロジーズ インコーポレイティド | 不斉ヒドロホルミル化プロセス |
| US7750168B2 (en) * | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5171892A (en) * | 1991-07-02 | 1992-12-15 | E. I. Du Pont De Nemours And Company | Chiral phospholanes via chiral 1,4-diol cyclic sulfates |
| DE4141299C2 (de) | 1991-12-14 | 2000-09-21 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von tertiären Phosphanen |
| US5399771A (en) | 1994-06-01 | 1995-03-21 | Merck & Co., Inc. | Process of synthesizing binaphthyl derivatives |
| DE69715418T2 (de) | 1996-07-15 | 2003-04-17 | Chirotech Technology Ltd., Cambridge | Liganden für asymmetrische katalysen |
-
1998
- 1998-05-11 US US09/530,845 patent/US6545183B1/en not_active Expired - Lifetime
- 1998-11-05 EP EP98952862A patent/EP1028967B1/en not_active Expired - Lifetime
- 1998-11-05 CA CA002307192A patent/CA2307192A1/en not_active Abandoned
- 1998-11-05 JP JP2000520453A patent/JP4397524B2/ja not_active Expired - Fee Related
- 1998-11-05 WO PCT/GB1998/003321 patent/WO1999024444A1/en not_active Ceased
- 1998-11-05 AU AU10410/99A patent/AU1041099A/en not_active Abandoned
- 1998-11-05 AT AT98952862T patent/ATE206128T1/de not_active IP Right Cessation
- 1998-11-05 ES ES98952862T patent/ES2162473T3/es not_active Expired - Lifetime
- 1998-11-05 DE DE69801841T patent/DE69801841T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE206128T1 (de) | 2001-10-15 |
| CA2307192A1 (en) | 1999-05-20 |
| DE69801841T2 (de) | 2002-05-16 |
| WO1999024444A1 (en) | 1999-05-20 |
| DE69801841D1 (de) | 2001-10-31 |
| US6545183B1 (en) | 2003-04-08 |
| JP2001522855A (ja) | 2001-11-20 |
| ES2162473T3 (es) | 2001-12-16 |
| EP1028967A1 (en) | 2000-08-23 |
| AU1041099A (en) | 1999-05-31 |
| EP1028967B1 (en) | 2001-09-26 |
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