JP2003252884A5 - - Google Patents
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- JP2003252884A5 JP2003252884A5 JP2002248058A JP2002248058A JP2003252884A5 JP 2003252884 A5 JP2003252884 A5 JP 2003252884A5 JP 2002248058 A JP2002248058 A JP 2002248058A JP 2002248058 A JP2002248058 A JP 2002248058A JP 2003252884 A5 JP2003252884 A5 JP 2003252884A5
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- JP
- Japan
- Prior art keywords
- hydrogen
- same
- different
- general formula
- substituent
- 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.)
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 150000002430 hydrocarbons Chemical group 0.000 claims description 13
- -1 alcohol compound Chemical class 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 229940126062 Compound A Drugs 0.000 claims description 4
- 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 4
- 239000012327 Ruthenium complex Substances 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 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 2
- 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 2
- WDYGPMAMBXJESZ-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)(C(N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical compound C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- REBJSIWYFWFTMF-UHFFFAOYSA-N C1(=CC=C(C=C1)P(C(C(C(C1=CC=CC=C1)P(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C)C1=CC=CC=C1)C1=CC=C(C=C1)C)C.C1(=CC=CC=C1)P(C(C(C(C1=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)C)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)P(C(C(C(C1=CC=CC=C1)P(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C)C1=CC=CC=C1)C1=CC=C(C=C1)C)C.C1(=CC=CC=C1)P(C(C(C(C1=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)C)C1=CC=CC=C1)C1=CC=CC=C1 REBJSIWYFWFTMF-UHFFFAOYSA-N 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 150000001450 anions Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 235000013847 iso-butane Nutrition 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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 1
- 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 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- UVNZNIGDKACWAA-UHFFFAOYSA-N [Ru].C1CC=CCCC=C1 Chemical compound [Ru].C1CC=CCCC=C1 UVNZNIGDKACWAA-UHFFFAOYSA-N 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| CA002414265A CA2414265A1 (en) | 2001-12-28 | 2002-12-16 | Novel ruthenium complexes and process for preparing alcoholic compounds using these |
| EP02028791A EP1323724B1 (en) | 2001-12-28 | 2002-12-23 | Ruthenium complexes and process for preparing alcoholic compounds using these |
| DE60218807T DE60218807T2 (de) | 2001-12-28 | 2002-12-23 | Rutheniumkomplexe und deren Verwendung zur Herstellung von Alkoholen |
| US10/330,501 US6790973B2 (en) | 2001-12-28 | 2002-12-27 | Ruthenium complexes and process for preparing alcoholic compounds using these |
Applications Claiming Priority (3)
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003252884A JP2003252884A (ja) | 2003-09-10 |
| JP3566955B2 JP3566955B2 (ja) | 2004-09-15 |
| JP2003252884A5 true JP2003252884A5 (enExample) | 2004-12-16 |
Family
ID=26625402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002248058A Expired - Lifetime 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 |
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
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