AU2006205652B2 - Metallocene-based phosphorus chiral phosphines - Google Patents
Metallocene-based phosphorus chiral phosphines Download PDFInfo
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- AU2006205652B2 AU2006205652B2 AU2006205652A AU2006205652A AU2006205652B2 AU 2006205652 B2 AU2006205652 B2 AU 2006205652B2 AU 2006205652 A AU2006205652 A AU 2006205652A AU 2006205652 A AU2006205652 A AU 2006205652A AU 2006205652 B2 AU2006205652 B2 AU 2006205652B2
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- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 27
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 24
- 239000011574 phosphorus Substances 0.000 title claims description 24
- 150000003003 phosphines Chemical class 0.000 title description 3
- 239000003446 ligand Substances 0.000 claims abstract description 51
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052785 arsenic Inorganic materials 0.000 claims abstract description 10
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- -1 carbocyclic aryl Chemical group 0.000 claims abstract description 6
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims abstract description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 239000010948 rhodium Substances 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Chemical group 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003732 xanthenes Chemical class 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000005984 hydrogenation reaction Methods 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000758 substrate Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 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 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- VPJJDEYLAURBLW-GXDHUFHOSA-N (2e)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methylidene]-3-methylbutanoic acid Chemical compound COCCCOC1=CC(\C=C(/C(C)C)C(O)=O)=CC=C1OC VPJJDEYLAURBLW-GXDHUFHOSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- CASDFPAHUXKYDO-UHFFFAOYSA-N [Li][C-]1C=CC=C1.[C-]1(C=CC=C1)[Li].[Fe+2] Chemical compound [Li][C-]1C=CC=C1.[C-]1(C=CC=C1)[Li].[Fe+2] CASDFPAHUXKYDO-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001212 derivatisation Methods 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- SZXUFLXBJGFODO-AWEZNQCLSA-N (2s)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutanoic acid Chemical compound COCCCOC1=CC(C[C@@H](C(C)C)C(O)=O)=CC=C1OC SZXUFLXBJGFODO-AWEZNQCLSA-N 0.000 description 2
- STRUEWADWBLLKY-PDGQHHTCSA-N (z)-2-ethoxy-3-(4-methoxy-3-phenylmethoxyphenyl)prop-2-enoic acid Chemical compound CCO\C(C(O)=O)=C/C1=CC=C(OC)C(OCC=2C=CC=CC=2)=C1 STRUEWADWBLLKY-PDGQHHTCSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- SZXUFLXBJGFODO-CQSZACIVSA-N (2r)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutanoic acid Chemical compound COCCCOC1=CC(C[C@H](C(C)C)C(O)=O)=CC=C1OC SZXUFLXBJGFODO-CQSZACIVSA-N 0.000 description 1
- MUAAFWXJBHEIKP-NSHDSACASA-N (2s)-2-ethoxy-3-(3-methoxyphenyl)propanoic acid Chemical compound CCO[C@H](C(O)=O)CC1=CC=CC(OC)=C1 MUAAFWXJBHEIKP-NSHDSACASA-N 0.000 description 1
- XMZMGCWYBUPKFB-SFHVURJKSA-N (2s)-2-ethoxy-3-(4-methoxy-3-phenylmethoxyphenyl)propanoic acid Chemical compound CCO[C@H](C(O)=O)CC1=CC=C(OC)C(OCC=2C=CC=CC=2)=C1 XMZMGCWYBUPKFB-SFHVURJKSA-N 0.000 description 1
- KVSIEUZWEVATDK-FLIBITNWSA-N (z)-2-ethoxy-3-(3-methoxyphenyl)prop-2-enoic acid Chemical compound CCO\C(C(O)=O)=C/C1=CC=CC(OC)=C1 KVSIEUZWEVATDK-FLIBITNWSA-N 0.000 description 1
- UJVNBIQMAHLIQW-VURMDHGXSA-N (z)-2-ethoxy-3-thiophen-2-ylprop-2-enoic acid Chemical compound CCO\C(C(O)=O)=C/C1=CC=CS1 UJVNBIQMAHLIQW-VURMDHGXSA-N 0.000 description 1
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 description 1
- ANUJXWUVZHMJDL-UHFFFAOYSA-N 1-bromocyclopenta-1,3-diene;iron(2+) Chemical compound [Fe+2].BrC1=CC=C[CH-]1.BrC1=CC=C[CH-]1 ANUJXWUVZHMJDL-UHFFFAOYSA-N 0.000 description 1
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- CQOUHPWMFZEXMO-UHFFFAOYSA-N 2,3-dibromo-1-(2,3-dibromo-4-methylphenoxy)-4-methylbenzene Chemical compound BrC1=C(Br)C(C)=CC=C1OC1=CC=C(C)C(Br)=C1Br CQOUHPWMFZEXMO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- WVTIKAMTGJUOSB-UHFFFAOYSA-N O1C2=C([Li])C=C(C(C)(C)C)C=C2C(C)(C)C2=C1C([Li])=CC(C(C)(C)C)=C2 Chemical compound O1C2=C([Li])C=C(C(C)(C)C)C=C2C(C)(C)C2=C1C([Li])=CC(C(C)(C)C)=C2 WVTIKAMTGJUOSB-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 238000006579 Tsuji-Trost allylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- UNMQCGHIBZALKM-YCBDHFTFSA-N cyclopenta-1,3-diene;(1r)-1-cyclopenta-2,4-dien-1-yl-n,n-dimethylethanamine;iron(2+) Chemical compound [Fe+2].C=1C=C[CH-]C=1.CN(C)[C@H](C)C1=CC=C[CH-]1 UNMQCGHIBZALKM-YCBDHFTFSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
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- 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
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- 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
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
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- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0500702.6 | 2005-01-14 | ||
| GBGB0500702.6A GB0500702D0 (en) | 2005-01-14 | 2005-01-14 | Novel metallocene-based phosphorus chiral phosphines |
| PCT/GB2006/000114 WO2006075166A1 (en) | 2005-01-14 | 2006-01-13 | Metallocene-based phosphorus chiral phosphines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006205652A1 AU2006205652A1 (en) | 2006-07-20 |
| AU2006205652B2 true AU2006205652B2 (en) | 2010-09-09 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006205652A Active AU2006205652B2 (en) | 2005-01-14 | 2006-01-13 | Metallocene-based phosphorus chiral phosphines |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7906669B2 (enExample) |
| EP (1) | EP1844061B1 (enExample) |
| JP (1) | JP5112881B2 (enExample) |
| CN (1) | CN101120010B (enExample) |
| AT (1) | ATE476437T1 (enExample) |
| AU (1) | AU2006205652B2 (enExample) |
| CA (1) | CA2594893C (enExample) |
| DE (1) | DE602006015910D1 (enExample) |
| ES (1) | ES2348060T3 (enExample) |
| GB (2) | GB0500702D0 (enExample) |
| WO (1) | WO2006075166A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5320283B2 (ja) * | 2006-04-12 | 2013-10-23 | ソルヴィーアス アクチェンゲゼルシャフト | フェロセンジホスフィン |
| WO2008055942A1 (en) * | 2006-11-10 | 2008-05-15 | Solvias Ag | Preparation of optically pure ferrocenediphosphines |
| EP2125210A1 (en) * | 2007-02-20 | 2009-12-02 | Solvias AG | Bis (ferrocenylphosphino) ferrocene ligands used in asymmetric hydrogenation reactions |
| US9394326B2 (en) * | 2011-08-08 | 2016-07-19 | Novomer, Inc. | Catalysts and methods for polymer synthesis |
| CN116120378B (zh) * | 2021-11-15 | 2025-06-06 | 中国科学院上海有机化学研究所 | 一种二茂铁双齿膦配体催化丁二烯制备己二腈的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001236912A1 (en) * | 2000-02-10 | 2001-08-20 | The Penn State Research Foundation | Chiral ferrocene phosphines and their use in asymmetric catalytic reactions |
| JP2005041847A (ja) | 2003-07-25 | 2005-02-17 | Nippon Chem Ind Co Ltd | フェロセンを置換基に有する光学活性リンキラルジホスフィン化合物、該化合物の中間体、該化合物の製造方法及び該化合物を用いる不斉合成反応、並びに該化合物を配位子として有する金属錯体触媒及び該金属錯体触媒を用いる不斉合成反応をする方法 |
| GB0400720D0 (en) | 2004-01-14 | 2004-02-18 | Stylacats Ltd | Novel ferrocene-based phosphorus chiral phosphines |
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2005
- 2005-01-14 GB GBGB0500702.6A patent/GB0500702D0/en not_active Ceased
-
2006
- 2006-01-13 WO PCT/GB2006/000114 patent/WO2006075166A1/en not_active Ceased
- 2006-01-13 GB GB0600713A patent/GB2422604A/en not_active Withdrawn
- 2006-01-13 CA CA2594893A patent/CA2594893C/en active Active
- 2006-01-13 JP JP2007550840A patent/JP5112881B2/ja active Active
- 2006-01-13 DE DE602006015910T patent/DE602006015910D1/de active Active
- 2006-01-13 AT AT06700701T patent/ATE476437T1/de active
- 2006-01-13 AU AU2006205652A patent/AU2006205652B2/en active Active
- 2006-01-13 CN CN200680004909.8A patent/CN101120010B/zh active Active
- 2006-01-13 US US11/813,987 patent/US7906669B2/en active Active
- 2006-01-13 EP EP06700701A patent/EP1844061B1/en active Active
- 2006-01-13 ES ES06700701T patent/ES2348060T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006075166A1 (en) | 2006-07-20 |
| GB2422604A (en) | 2006-08-02 |
| CA2594893C (en) | 2014-05-13 |
| GB0500702D0 (en) | 2005-02-23 |
| JP2008526938A (ja) | 2008-07-24 |
| AU2006205652A1 (en) | 2006-07-20 |
| CA2594893A1 (en) | 2006-07-20 |
| ATE476437T1 (de) | 2010-08-15 |
| CN101120010A (zh) | 2008-02-06 |
| JP5112881B2 (ja) | 2013-01-09 |
| DE602006015910D1 (de) | 2010-09-16 |
| US20090137824A1 (en) | 2009-05-28 |
| EP1844061A1 (en) | 2007-10-17 |
| US7906669B2 (en) | 2011-03-15 |
| ES2348060T3 (es) | 2010-11-29 |
| CN101120010B (zh) | 2013-07-03 |
| EP1844061B1 (en) | 2010-08-04 |
| GB0600713D0 (en) | 2006-02-22 |
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