NO744324L - - Google Patents
Info
- Publication number
- NO744324L NO744324L NO744324A NO744324A NO744324L NO 744324 L NO744324 L NO 744324L NO 744324 A NO744324 A NO 744324A NO 744324 A NO744324 A NO 744324A NO 744324 L NO744324 L NO 744324L
- Authority
- NO
- Norway
- Prior art keywords
- catalyst
- bis
- rhodium
- optically active
- specified
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 claims description 101
- 238000000034 method Methods 0.000 claims description 47
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 43
- 239000010948 rhodium Substances 0.000 claims description 42
- 229910052703 rhodium Inorganic materials 0.000 claims description 39
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000003446 ligand Substances 0.000 claims description 25
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- -1 phospho atom Chemical group 0.000 claims description 21
- 230000003287 optical effect Effects 0.000 claims description 20
- 229910052723 transition metal Inorganic materials 0.000 claims description 20
- 150000003624 transition metals Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- GKZIPAQOHJQRTP-UHFFFAOYSA-N (2-methoxyphenyl)methyl-[2-[(2-methoxyphenyl)methyl-phenylphosphanyl]ethyl]-phenylphosphane Chemical compound COC1=CC=CC=C1CP(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)CC1=CC=CC=C1OC GKZIPAQOHJQRTP-UHFFFAOYSA-N 0.000 claims description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 12
- 229910052741 iridium Inorganic materials 0.000 claims description 12
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052707 ruthenium Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000002091 cationic group Chemical group 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 7
- 150000004696 coordination complex Chemical class 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004437 phosphorous atom Chemical group 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- HCAJAVWKBZKSHA-UHFFFAOYSA-N (2-methoxyphenyl)methyl-phenylphosphane Chemical compound COC1=CC=CC=C1CPC1=CC=CC=C1 HCAJAVWKBZKSHA-UHFFFAOYSA-N 0.000 claims description 2
- PJXFVEDMOFFYNO-UHFFFAOYSA-N cyclohexyl-[2-[cyclohexyl-[(2-methoxyphenyl)methyl]phosphanyl]ethyl]-[(2-methoxyphenyl)methyl]phosphane Chemical compound COC1=CC=CC=C1CP(C1CCCCC1)CCP(C1CCCCC1)CC1=CC=CC=C1OC PJXFVEDMOFFYNO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- DHPLHVXCTYOIPW-UHFFFAOYSA-N 3-(2-methoxyphenyl)propyl-[2-[3-(2-methoxyphenyl)propylphosphanyl]ethyl]phosphane Chemical compound COC1=CC=CC=C1CCCPCCPCCCC1=CC=CC=C1OC DHPLHVXCTYOIPW-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000005984 hydrogenation reaction Methods 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000002243 precursor Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 150000003003 phosphines Chemical class 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- QFVPRARVHGWMOB-UHFFFAOYSA-N 1-methoxy-2-[[2-[(2-methoxyphenyl)methyl-phenylphosphoryl]ethyl-phenylphosphoryl]methyl]benzene Chemical compound COC1=CC=CC=C1CP(=O)(C=1C=CC=CC=1)CCP(=O)(C=1C=CC=CC=1)CC1=CC=CC=C1OC QFVPRARVHGWMOB-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 235000008206 alpha-amino acids Nutrition 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 4
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 150000001371 alpha-amino acids Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Chemical group 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000008729 phenylalanine Nutrition 0.000 description 4
- XODAOBAZOQSFDS-JXMROGBWSA-N (e)-2-acetamido-3-phenylprop-2-enoic acid Chemical compound CC(=O)N\C(C(O)=O)=C\C1=CC=CC=C1 XODAOBAZOQSFDS-JXMROGBWSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CBQJSKKFNMDLON-JTQLQIEISA-N N-acetyl-L-phenylalanine Chemical compound CC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-JTQLQIEISA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 229960005190 phenylalanine Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003283 rhodium Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 2
- 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
- QRBWWOWIHDNJFU-UHFFFAOYSA-N COC1=CC=CC=C1CCP(=O)C1=CC=CC=C1 Chemical compound COC1=CC=CC=C1CCP(=O)C1=CC=CC=C1 QRBWWOWIHDNJFU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
- 229960003767 alanine Drugs 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000003935 benzaldehydes Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
- 150000002994 phenylalanines Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- BRXHQQWBAFWUJN-UHFFFAOYSA-N (2-ethoxyphenyl)-[2-[(2-ethoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane Chemical compound CCOC1=CC=CC=C1P(C=1C=CC=CC=1)CCP(C=1C(=CC=CC=1)OCC)C1=CC=CC=C1 BRXHQQWBAFWUJN-UHFFFAOYSA-N 0.000 description 1
- YJSANCVXFYCZQN-UHFFFAOYSA-N (2-methoxyphenyl)methyl-[2-[(2-methoxyphenyl)methyl-(2-methylphenyl)phosphanyl]ethyl]-(2-methylphenyl)phosphane Chemical compound COC1=CC=CC=C1CP(C=1C(=CC=CC=1)C)CCP(C=1C(=CC=CC=1)C)CC1=CC=CC=C1OC YJSANCVXFYCZQN-UHFFFAOYSA-N 0.000 description 1
- DFEBNZHUHXUQNX-UHFFFAOYSA-N (2-methoxyphenyl)methyl-[2-[(2-methoxyphenyl)methyl-(3-phenylphenyl)phosphanyl]ethyl]-(3-phenylphenyl)phosphane Chemical compound COC1=CC=CC=C1CP(C=1C=C(C=CC=1)C=1C=CC=CC=1)CCP(C=1C=C(C=CC=1)C=1C=CC=CC=1)CC1=CC=CC=C1OC DFEBNZHUHXUQNX-UHFFFAOYSA-N 0.000 description 1
- UJQPKLUAKSBOCM-UHFFFAOYSA-N (2-methoxyphenyl)methyl-[2-[(2-methoxyphenyl)methyl-(4-methylphenyl)phosphanyl]ethyl]-(4-methylphenyl)phosphane Chemical compound COC1=CC=CC=C1CP(C=1C=CC(C)=CC=1)CCP(C=1C=CC(C)=CC=1)CC1=CC=CC=C1OC UJQPKLUAKSBOCM-UHFFFAOYSA-N 0.000 description 1
- MNHIXUDSHBLATR-UHFFFAOYSA-N (2-methoxyphenyl)methyl-[2-[(2-methoxyphenyl)methyl-(4-phenylphenyl)phosphanyl]ethyl]-(4-phenylphenyl)phosphane Chemical compound COC1=CC=CC=C1CP(C=1C=CC(=CC=1)C=1C=CC=CC=1)CCP(C=1C=CC(=CC=1)C=1C=CC=CC=1)CC1=CC=CC=C1OC MNHIXUDSHBLATR-UHFFFAOYSA-N 0.000 description 1
- RIMMHDSDDRRHDT-UHFFFAOYSA-N (2-methoxyphenyl)methyl-[2-[(2-methoxyphenyl)methylphosphanyl]ethyl]phosphane Chemical compound COC1=CC=CC=C1CPCCPCC1=CC=CC=C1OC RIMMHDSDDRRHDT-UHFFFAOYSA-N 0.000 description 1
- XUOZEEVSVMGBSB-FVGYRXGTSA-N (2s)-2-acetamido-3-(4-hydroxy-3-methoxyphenyl)propanoic acid;acetic acid Chemical compound CC(O)=O.COC1=CC(C[C@H](NC(C)=O)C(O)=O)=CC=C1O XUOZEEVSVMGBSB-FVGYRXGTSA-N 0.000 description 1
- VKPPWSJKBRRRGY-UHFFFAOYSA-N (3-chlorophenyl)-[2-[(3-chlorophenyl)-[(2-methoxyphenyl)methyl]phosphanyl]ethyl]-[(2-methoxyphenyl)methyl]phosphane Chemical compound COC1=CC=CC=C1CP(C=1C=C(Cl)C=CC=1)CCP(C=1C=C(Cl)C=CC=1)CC1=CC=CC=C1OC VKPPWSJKBRRRGY-UHFFFAOYSA-N 0.000 description 1
- IKBPBSYMLDMCOA-UHFFFAOYSA-N (3-ethylphenyl)-[2-[(3-ethylphenyl)-[(2-methoxyphenyl)methyl]phosphanyl]ethyl]-[(2-methoxyphenyl)methyl]phosphane Chemical compound CCC1=CC=CC(P(CCP(CC=2C(=CC=CC=2)OC)C=2C=C(CC)C=CC=2)CC=2C(=CC=CC=2)OC)=C1 IKBPBSYMLDMCOA-UHFFFAOYSA-N 0.000 description 1
- JIEXTPXEPQZRLM-UHFFFAOYSA-N (4-bromophenyl)-[2-[(4-bromophenyl)-[(2-methoxyphenyl)methyl]phosphanyl]ethyl]-[(2-methoxyphenyl)methyl]phosphane Chemical compound COC1=CC=CC=C1CP(C=1C=CC(Br)=CC=1)CCP(C=1C=CC(Br)=CC=1)CC1=CC=CC=C1OC JIEXTPXEPQZRLM-UHFFFAOYSA-N 0.000 description 1
- NPQHFNMMJHXBEL-UHFFFAOYSA-N (4-chlorophenyl)-[2-[(4-chlorophenyl)-[(2-methoxyphenyl)methyl]phosphanyl]ethyl]-[(2-methoxyphenyl)methyl]phosphane Chemical compound COC1=CC=CC=C1CP(C=1C=CC(Cl)=CC=1)CCP(C=1C=CC(Cl)=CC=1)CC1=CC=CC=C1OC NPQHFNMMJHXBEL-UHFFFAOYSA-N 0.000 description 1
- AXJPMJHFAOBHIB-UHFFFAOYSA-N (4-ethylphenyl)-[2-[(4-ethylphenyl)-[(2-methoxyphenyl)methyl]phosphanyl]ethyl]-[(2-methoxyphenyl)methyl]phosphane Chemical compound C1=CC(CC)=CC=C1P(CC=1C(=CC=CC=1)OC)CCP(C=1C=CC(CC)=CC=1)CC1=CC=CC=C1OC AXJPMJHFAOBHIB-UHFFFAOYSA-N 0.000 description 1
- ZHWRJWKCEPKHHF-UHFFFAOYSA-N (5-bromo-2-methoxyphenyl)-[2-[(5-bromo-2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane Chemical compound COC1=CC=C(Br)C=C1P(C=1C=CC=CC=1)CCP(C=1C(=CC=C(Br)C=1)OC)C1=CC=CC=C1 ZHWRJWKCEPKHHF-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- OVIINTUWRZTCLC-UHFFFAOYSA-N 1-[[cyclohexyl-[2-[cyclohexyl-[(2-methoxyphenyl)methyl]phosphoryl]ethyl]phosphoryl]methyl]-2-methoxybenzene Chemical compound COC1=CC=CC=C1CP(=O)(C1CCCCC1)CCP(=O)(C1CCCCC1)CC1=CC=CC=C1OC OVIINTUWRZTCLC-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-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
- SOMMFGSFLILBJJ-UHFFFAOYSA-N 2-acetamido-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid;acetic acid Chemical group CC(O)=O.COC1=CC(C=C(NC(C)=O)C(O)=O)=CC=C1O SOMMFGSFLILBJJ-UHFFFAOYSA-N 0.000 description 1
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VSFLHLFFNNDRLJ-UHFFFAOYSA-N COC1=CC=CC=C1CCCP(=O)CCP(=O)CCCC1=CC=CC=C1OC Chemical compound COC1=CC=CC=C1CCCP(=O)CCP(=O)CCCC1=CC=CC=C1OC VSFLHLFFNNDRLJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NIGWMJHCCYYCSF-UHFFFAOYSA-N Fenclonine Chemical compound OC(=O)C(N)CC1=CC=C(Cl)C=C1 NIGWMJHCCYYCSF-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
- B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
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Applications Claiming Priority (2)
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US42146373A | 1973-12-03 | 1973-12-03 | |
US05/514,987 US4008281A (en) | 1973-12-03 | 1974-10-15 | Asymmetric catalysis |
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NO744324L true NO744324L (pt) | 1975-06-30 |
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NO802008A NO802008L (no) | 1973-12-03 | 1980-07-03 | Optisk aktive bisfosfinforbindelser for anvendelse i optisk aktive hydrogeneringskatalysatorer |
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US (2) | US4008281A (pt) |
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CH (1) | CH601142A5 (pt) |
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NO (2) | NO744324L (pt) |
PL (1) | PL107722B1 (pt) |
RO (1) | RO72485A (pt) |
SE (2) | SE421316B (pt) |
SU (1) | SU663273A3 (pt) |
YU (1) | YU318874A (pt) |
Families Citing this family (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4124533A (en) * | 1971-03-08 | 1978-11-07 | Monsanto Company | Metal coordination complexes containing optically active phosphine or arsine ligands |
HU177239B (hu) * | 1974-10-15 | 1981-08-28 | Monsanto Co | Eljárás N-acetamido-L-alanin-származékok előállítására α-acetamido-akrilsav-származékok aszimmetrikus katalitikus hídrogénezésével |
US4515731A (en) * | 1975-08-25 | 1985-05-07 | Monsanto Company | Asymmetric catalysis |
US4123465A (en) * | 1975-10-16 | 1978-10-31 | Hoffmann-La Roche Inc. | Chiral tertiary phosphines |
US4166824A (en) * | 1977-06-14 | 1979-09-04 | American Cyanamid Company | Chiral rhodium-diphosphine catalyst capable of catalytic reduction of a tetramisole precursor to give a significant excess of the desired S-(-)isomer, levamisole |
US4120870A (en) * | 1977-07-18 | 1978-10-17 | Hoffmann-La Roche Inc. | Metal phosphine complex |
IT1087963B (it) * | 1977-10-17 | 1985-06-04 | Snam Progetti | Idrogenazione asimmetrica di olefine prochirali mediante complessi di metalli di transazione immobilizzati in minerali argillosi. |
US5147868A (en) * | 1978-07-24 | 1992-09-15 | Merck & Co., Inc. | Thienamycin renal peptidase inhibitors |
ZA793744B (en) * | 1978-07-24 | 1981-02-25 | Merck & Co Inc | Z-2-acylamino-3-monsosubstituted propenoates |
US4616038A (en) * | 1978-07-24 | 1986-10-07 | Merck & Co., Inc. | Combination of thienamycin-type antibiotics with dipeptidase inhibitors |
US4880793A (en) * | 1978-07-24 | 1989-11-14 | Merck & Co., Inc. | Combination of thienamycin-type antibiotics with dipeptidase inhibitors |
DE3034353A1 (de) * | 1979-02-12 | 1981-03-26 | Exxon Research Engineering Co | Tetraalkyl phosphonium substituted transition metal complexes |
US4302401A (en) * | 1980-01-23 | 1981-11-24 | Exxon Research & Engineering Co. | Tetraalkyl phosphonium substituted phosphine and amine transition metal complexes |
US4204997A (en) * | 1979-03-19 | 1980-05-27 | Monsanto Company | Asymmetric amination of 1,3-dienes |
US4539208A (en) * | 1980-09-17 | 1985-09-03 | Merck & Co., Inc. | Combination of thienamycin-type antibiotics with dipeptidase inhibitors |
DE3000445C2 (de) * | 1980-01-08 | 1982-12-02 | Degussa Ag, 6000 Frankfurt | Rhodiumkomplexe und deren Verwendung |
US4473505A (en) * | 1980-02-12 | 1984-09-25 | Exxon Research And Engineering Co. | Phosphine and phosphonium compounds and catalysts |
US4331818A (en) * | 1980-03-19 | 1982-05-25 | The Procter & Gamble Company | Chiral phospine ligand |
DE3018388A1 (de) * | 1980-05-14 | 1981-11-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von optisch aktiven verbindungen und deren verwendung zur herstellung von vitamin e |
DE3039053C2 (de) * | 1980-10-16 | 1984-05-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dipeptiden |
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FR2230654B1 (pt) * | 1973-05-21 | 1975-11-21 | Rhone Poulenc Ind |
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1974
- 1974-10-15 US US05/514,987 patent/US4008281A/en not_active Expired - Lifetime
- 1974-11-22 IL IL7446108A patent/IL46108A/xx unknown
- 1974-11-29 NL NL7415583.A patent/NL166692C/xx not_active IP Right Cessation
- 1974-12-02 BR BR10074/74A patent/BR7410074A/pt unknown
- 1974-12-02 NO NO744324A patent/NO744324L/no unknown
- 1974-12-02 DE DE2463010A patent/DE2463010C2/de not_active Expired
- 1974-12-02 HU HU74MO00000927A patent/HU172991B/hu unknown
- 1974-12-02 MX MX170589A patent/MX149399A/es unknown
- 1974-12-02 YU YU03188/74A patent/YU318874A/xx unknown
- 1974-12-02 IT IT3008774A patent/IT1026717B/it active
- 1974-12-02 GB GB5201774A patent/GB1466803A/en not_active Expired
- 1974-12-02 SE SE7415029A patent/SE421316B/xx unknown
- 1974-12-02 PL PL1974176129A patent/PL107722B1/pl unknown
- 1974-12-02 RO RO7480666A patent/RO72485A/ro unknown
- 1974-12-02 DE DE2456937A patent/DE2456937C3/de not_active Expired
- 1974-12-02 FI FI3487/74A patent/FI60215C/fi active
- 1974-12-02 CH CH1593974A patent/CH601142A5/xx not_active IP Right Cessation
- 1974-12-02 BE BE151066A patent/BE822848A/xx not_active IP Right Cessation
- 1974-12-02 MX MX742888U patent/MX5144E/es unknown
- 1974-12-02 DK DK625274AA patent/DK139873B/da not_active IP Right Cessation
- 1974-12-02 FR FR7439420A patent/FR2253026B1/fr not_active Expired
- 1974-12-02 MX MX170590A patent/MX148257A/es unknown
- 1974-12-02 CA CA215,181A patent/CA1051912A/en not_active Expired
- 1974-12-02 JP JP13708774A patent/JPS5410352B2/ja not_active Expired
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1975
- 1975-08-21 SU SU752163234A patent/SU663273A3/ru active
-
1976
- 1976-06-03 DK DK245476A patent/DK245476A/da not_active Application Discontinuation
- 1976-06-03 DK DK245376A patent/DK245376A/da not_active Application Discontinuation
-
1977
- 1977-06-27 IN IN958/CAL/77A patent/IN145550B/en unknown
- 1977-06-27 IN IN957/CAL/77A patent/IN145549B/en unknown
-
1978
- 1978-07-31 US US05/929,635 patent/US4220590A/en not_active Expired - Lifetime
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1980
- 1980-07-03 NO NO802008A patent/NO802008L/no unknown
- 1980-07-17 FI FI802271A patent/FI63216C/fi not_active IP Right Cessation
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1981
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