CA2414265A1 - Novel ruthenium complexes and process for preparing alcoholic compounds using these - Google Patents
Novel ruthenium complexes and process for preparing alcoholic compounds using these Download PDFInfo
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- CA2414265A1 CA2414265A1 CA002414265A CA2414265A CA2414265A1 CA 2414265 A1 CA2414265 A1 CA 2414265A1 CA 002414265 A CA002414265 A CA 002414265A CA 2414265 A CA2414265 A CA 2414265A CA 2414265 A1 CA2414265 A1 CA 2414265A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 55
- 230000001476 alcoholic effect Effects 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 150000003303 ruthenium Chemical class 0.000 title abstract description 19
- -1 diphosphine compound Chemical class 0.000 claims abstract description 133
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 114
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 109
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 109
- 239000012327 Ruthenium complex Substances 0.000 claims abstract description 64
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 43
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 27
- 150000001450 anions Chemical group 0.000 claims abstract description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 21
- 238000006243 chemical reaction Methods 0.000 claims description 106
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- 229940126062 Compound A Drugs 0.000 claims description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical group C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- WREFXNGPCLHVSW-UHFFFAOYSA-N (4-diphenylphosphanyl-3-methylpentan-2-yl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 WREFXNGPCLHVSW-UHFFFAOYSA-N 0.000 claims description 5
- WDYGPMAMBXJESZ-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical group C1=CC(OC)=CC=C1C(N)(C(N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-UHFFFAOYSA-N 0.000 claims description 5
- BQUNSIYVDVZZEA-UHFFFAOYSA-N 4-bis(3,5-dimethylphenyl)phosphanylpentan-2-yl-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)CC(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 BQUNSIYVDVZZEA-UHFFFAOYSA-N 0.000 claims description 5
- ATHCDBOOSFQXPT-UHFFFAOYSA-N [3-bis(3,5-dimethylphenyl)phosphanyl-1,3-diphenylpropyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(P(C(CC(P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)=C1 ATHCDBOOSFQXPT-UHFFFAOYSA-N 0.000 claims description 5
- GFGZHQCWZWATGF-UHFFFAOYSA-N [3-bis(4-methylphenyl)phosphanyl-1,3-diphenylpropyl]-bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)CC(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GFGZHQCWZWATGF-UHFFFAOYSA-N 0.000 claims description 5
- YOHVTQHWOPUYGB-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3-methylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 YOHVTQHWOPUYGB-UHFFFAOYSA-N 0.000 claims description 5
- WPEXKMAYUSUXIF-UHFFFAOYSA-N (3-diphenylphosphanyl-1,3-diphenylpropyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)CC(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 WPEXKMAYUSUXIF-UHFFFAOYSA-N 0.000 claims description 4
- ZHIOKCFUZLQANC-UHFFFAOYSA-N 4-bis(4-methylphenyl)phosphanylpentan-2-yl-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)CC(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZHIOKCFUZLQANC-UHFFFAOYSA-N 0.000 claims description 4
- LVYGXVVRZGNPMS-UHFFFAOYSA-N [4-bis(4-methylphenyl)phosphanyl-3-methylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LVYGXVVRZGNPMS-UHFFFAOYSA-N 0.000 claims description 4
- KORFDERLECDIGW-UHFFFAOYSA-N (3-diphenylphosphanyl-2-methyl-1,3-diphenylpropyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(C)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 KORFDERLECDIGW-UHFFFAOYSA-N 0.000 claims description 2
- UXHGOSLRMLRAKR-UHFFFAOYSA-N [3-bis(3,5-dimethylphenyl)phosphanyl-2-methyl-1,3-diphenylpropyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 UXHGOSLRMLRAKR-UHFFFAOYSA-N 0.000 claims description 2
- RVNVDLRZOHJDCB-UHFFFAOYSA-N [3-bis(4-methylphenyl)phosphanyl-2-methyl-1,3-diphenylpropyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RVNVDLRZOHJDCB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 53
- VURFVHCLMJOLKN-UHFFFAOYSA-N Diphosphine Natural products PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 abstract description 48
- 239000003446 ligand Substances 0.000 abstract description 31
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 abstract description 20
- 230000009257 reactivity Effects 0.000 abstract description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 102
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 87
- 229910052717 sulfur Inorganic materials 0.000 description 71
- 229910052786 argon Inorganic materials 0.000 description 51
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 48
- 239000012295 chemical reaction liquid Substances 0.000 description 46
- 230000003287 optical effect Effects 0.000 description 41
- WDYGPMAMBXJESZ-GOSISDBHSA-N (2r)-1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)([C@H](N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-GOSISDBHSA-N 0.000 description 39
- HBIHVBJJZAHVLE-UHFFFAOYSA-L dibromoruthenium Chemical compound Br[Ru]Br HBIHVBJJZAHVLE-UHFFFAOYSA-L 0.000 description 39
- 150000002430 hydrocarbons Chemical group 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000002904 solvent Substances 0.000 description 35
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000011521 glass Substances 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 238000004817 gas chromatography Methods 0.000 description 21
- 239000000758 substrate Substances 0.000 description 21
- 238000005984 hydrogenation reaction Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 14
- 229910052707 ruthenium Inorganic materials 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 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 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical class [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 9
- WDYGPMAMBXJESZ-SFHVURJKSA-N (2s)-1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)([C@@H](N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-SFHVURJKSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 7
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 6
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229940073584 methylene chloride Drugs 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 6
- 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 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 5
- 125000003884 phenylalkyl group Chemical group 0.000 description 5
- 150000003304 ruthenium compounds Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- DAVFJRVIVZOKKS-UHFFFAOYSA-N 2-(4-methylphenyl)ethanol Chemical compound CC1=CC=C(CCO)C=C1 DAVFJRVIVZOKKS-UHFFFAOYSA-N 0.000 description 4
- GDWRKZLROIFUML-UHFFFAOYSA-N 4-phenylbutan-2-ol Chemical compound CC(O)CCC1=CC=CC=C1 GDWRKZLROIFUML-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- VEAFKIYNHVBNIP-UHFFFAOYSA-N 1,3-Diphenylpropane Chemical class C=1C=CC=CC=1CCCC1=CC=CC=C1 VEAFKIYNHVBNIP-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- FWXAUDSWDBGCMN-ZEQRLZLVSA-N chiraphos Chemical compound C=1C=CC=CC=1P([C@@H](C)[C@H](C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-ZEQRLZLVSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- GYZZZILPVUYAFJ-UHFFFAOYSA-N phanephos Chemical compound C1CC(C(=C2)P(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C2CCC2=CC=C1C=C2P(C=1C=CC=CC=1)C1=CC=CC=C1 GYZZZILPVUYAFJ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- PONXTPCRRASWKW-UHFFFAOYSA-N 1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)C(N)C1=CC=CC=C1 PONXTPCRRASWKW-UHFFFAOYSA-N 0.000 description 2
- UABXUIWIFUZYQK-UHFFFAOYSA-N 1-(furan-2-yl)ethanol Chemical compound CC(O)C1=CC=CO1 UABXUIWIFUZYQK-UHFFFAOYSA-N 0.000 description 2
- JMSUNAQVHOHLMX-UHFFFAOYSA-N 1-cyclohexylethanol Chemical compound CC(O)C1CCCCC1 JMSUNAQVHOHLMX-UHFFFAOYSA-N 0.000 description 2
- WUNFIVTVJXZDDJ-UHFFFAOYSA-N 1-thiophen-2-ylethanol Chemical compound CC(O)C1=CC=CS1 WUNFIVTVJXZDDJ-UHFFFAOYSA-N 0.000 description 2
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 2
- CTYPJIUQROQJBG-UHFFFAOYSA-N 4-diphenylphosphanylpentan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)CC(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 CTYPJIUQROQJBG-UHFFFAOYSA-N 0.000 description 2
- ULBXWWGWDPVHAO-UHFFFAOYSA-N Chlorbufam Chemical compound C#CC(C)OC(=O)NC1=CC=CC(Cl)=C1 ULBXWWGWDPVHAO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
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- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- GTBPUYSGSDIIMM-UHFFFAOYSA-N phosphane;ruthenium Chemical compound P.[Ru] GTBPUYSGSDIIMM-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000011924 stereoselective hydrogenation Methods 0.000 description 1
- 238000011916 stereoselective reduction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- 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
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001401170 | 2001-12-28 | ||
| JP2001-401170 | 2001-12-28 | ||
| JP2002248058A JP3566955B2 (ja) | 2001-12-28 | 2002-08-28 | 新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法 |
| JP2002-248058 | 2002-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2414265A1 true CA2414265A1 (en) | 2003-06-28 |
Family
ID=26625402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002414265A Abandoned CA2414265A1 (en) | 2001-12-28 | 2002-12-16 | Novel ruthenium complexes and process for preparing alcoholic compounds using these |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6790973B2 (enExample) |
| EP (1) | EP1323724B1 (enExample) |
| JP (1) | JP3566955B2 (enExample) |
| CA (1) | CA2414265A1 (enExample) |
| DE (1) | DE60218807T2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004101580A1 (ja) | 2003-05-19 | 2004-11-25 | Takeda Pharmaceutical Company Limited | ホスフィン-ボラン錯体の製造法 |
| GB0316439D0 (en) | 2003-07-15 | 2003-08-20 | Johnson Matthey Plc | Catalysts |
| DE602004030129D1 (de) * | 2003-07-31 | 2010-12-30 | Basf Se | Insektenfalle sowie verfahren zum fangen und aufbewahren von schadinsekten |
| ATE509024T1 (de) | 2003-08-13 | 2011-05-15 | Takasago Perfumery Co Ltd | Neuer übergangsmetallkomplex und verfahren zur herstellung von optisch aktivem alkohol mit dem komplex |
| JP5078608B2 (ja) | 2005-03-30 | 2012-11-21 | 関東化学株式会社 | 光学活性キヌクリジノール類の製造方法 |
| MX2009000616A (es) * | 2006-07-27 | 2009-01-28 | Hoffmann La Roche | Hidrogenacion asimetrica de 1,1,1-trifluoroacetona. |
| JP5172124B2 (ja) | 2006-09-29 | 2013-03-27 | 関東化学株式会社 | ２位に置換基を有する光学活性キヌクリジノール類の製造方法 |
| CN101541716B (zh) * | 2006-11-27 | 2012-10-03 | 弗门尼舍有限公司 | 通过钌/二齿配位体的络合物进行的酯的氢化 |
| CA2703671A1 (en) * | 2007-10-30 | 2009-05-07 | Kanata Chemical Technologies Inc. | Cationic transition metal catalysts |
| WO2009124897A1 (de) * | 2008-04-08 | 2009-10-15 | Basf Se | Komplexverbindung, enthaltend metallatom und phosphinderivat als ligand |
| JP5507931B2 (ja) * | 2009-09-01 | 2014-05-28 | 関東化学株式会社 | 芳香族複素環をもつ光学活性アルコールの製造方法 |
| DE102010002482B3 (de) | 2010-03-01 | 2012-01-05 | Technische Universität Braunschweig | Lumineszente Organometallverbindung |
| KR101808261B1 (ko) * | 2010-04-28 | 2017-12-12 | 다카사고 고료 고교 가부시키가이샤 | 루테늄 착체 및 광학적으로 활성인 알코올 화합물의 제조방법 |
| EP2578570A1 (en) * | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| JP6173702B2 (ja) * | 2012-02-01 | 2017-08-02 | 国立大学法人北海道大学 | 光学活性アミン化合物の製造方法 |
| JP6437187B2 (ja) * | 2013-07-26 | 2018-12-12 | 関東化學株式会社 | 光学活性２級アルコールの製造方法 |
| CN111320591B (zh) * | 2020-03-30 | 2023-03-31 | 陕西师范大学 | 一种合成手性γ-氨基醇的方法 |
| EP4516776A4 (en) * | 2022-04-26 | 2025-08-20 | Shenzhen Catalyst Tech Co Ltd | PROCESS FOR THE UNPROTECTED ASYMMETRIC PREPARATION OF NICOTINE |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2693190B1 (fr) * | 1992-07-02 | 1994-09-23 | Elf Aquitaine | Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO. |
| JP2731377B2 (ja) | 1994-12-07 | 1998-03-25 | 科学技術振興事業団 | 光学活性アルコール類の製造方法 |
| CA2164685C (en) | 1994-12-07 | 2005-03-08 | Takeshi Ohkuma | Method for producing an alcohol |
| JP4004123B2 (ja) | 1997-12-26 | 2007-11-07 | 独立行政法人科学技術振興機構 | ルテニウム錯体を触媒とするアルコール化合物の製造方法 |
| WO2001074829A1 (en) | 2000-03-30 | 2001-10-11 | Chirotech Technology Limited | Ruthenium-diphosphine complexes and their use as catalysts |
-
2002
- 2002-08-28 JP JP2002248058A patent/JP3566955B2/ja not_active Expired - Lifetime
- 2002-12-16 CA CA002414265A patent/CA2414265A1/en not_active Abandoned
- 2002-12-23 DE DE60218807T patent/DE60218807T2/de not_active Expired - Lifetime
- 2002-12-23 EP EP02028791A patent/EP1323724B1/en not_active Expired - Lifetime
- 2002-12-27 US US10/330,501 patent/US6790973B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003252884A (ja) | 2003-09-10 |
| EP1323724A3 (en) | 2003-09-24 |
| EP1323724B1 (en) | 2007-03-14 |
| US6790973B2 (en) | 2004-09-14 |
| DE60218807D1 (de) | 2007-04-26 |
| DE60218807T2 (de) | 2007-12-06 |
| US20030166978A1 (en) | 2003-09-04 |
| EP1323724A2 (en) | 2003-07-02 |
| JP3566955B2 (ja) | 2004-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |