CH624088A5 - Process for the preparation of enantiomorphs of acyloxypropionic acid derivatives with high optical purity - Google Patents

Process for the preparation of enantiomorphs of acyloxypropionic acid derivatives with high optical purity Download PDF

Info

Publication number: CH624088A5
Authority: CH; Switzerland
Prior art keywords: group; bis; carbon atoms; formula; optionally substituted
Prior art date: 1975-08-25

Application number

CH1070576A

Other languages

German (de)

English (en)

Inventor

Gerald Lee Bachman

Billy Dale Vineyard

Original Assignee

Monsanto Co

Priority date (The priority date 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 date listed.)

1975-08-25

Filing date

1976-08-24

Publication date

1981-07-15

1976-08-24 Application filed by Monsanto Co filed Critical Monsanto Co

1981-07-15 Publication of CH624088A5 publication Critical patent/CH624088A5/de

Links

230000003287 optical effect Effects 0.000 title claims description 25
238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 12
239000002253 acid Substances 0.000 title claims description 6
239000003054 catalyst Substances 0.000 claims description 34
239000003446 ligand Substances 0.000 claims description 24
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 18
-1 o-anisylphenyl Chemical group 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
229910052703 rhodium Inorganic materials 0.000 claims description 10
239000010948 rhodium Substances 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 9
239000002184 metal Substances 0.000 claims description 9
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
125000004437 phosphorous atom Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
229910052741 iridium Inorganic materials 0.000 claims description 3
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
229910052707 ruthenium Inorganic materials 0.000 claims description 3
150000004696 coordination complex Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
238000007172 homogeneous catalysis Methods 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims 3
125000003107 substituted aryl group Chemical group 0.000 claims 3
YUSJHYOMZBLZFY-UHFFFAOYSA-N 1-phenylprop-1-en-2-yl acetate Chemical compound CC(=O)OC(C)=CC1=CC=CC=C1 YUSJHYOMZBLZFY-UHFFFAOYSA-N 0.000 claims 1
125000004494 ethyl ester group Chemical group 0.000 claims 1
FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims 1
125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 16
150000001336 alkenes Chemical class 0.000 description 14
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 14
238000005984 hydrogenation reaction Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
239000000758 substrate Substances 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
238000009876 asymmetric hydrogenation reaction Methods 0.000 description 7
125000004429 atom Chemical group 0.000 description 7
239000000203 mixture Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
CAHPEYNELBHXTB-UHFFFAOYSA-N ethyl 3-acetyloxy-3-phenylprop-2-enoate Chemical compound CCOC(=O)C=C(OC(C)=O)C1=CC=CC=C1 CAHPEYNELBHXTB-UHFFFAOYSA-N 0.000 description 6
239000000376 reactant Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
125000002091 cationic group Chemical group 0.000 description 4
MHJYJCPZTDJIOT-UHFFFAOYSA-N ethyl 2-acetyloxy-3-phenylprop-2-enoate Chemical class CCOC(=O)C(OC(C)=O)=CC1=CC=CC=C1 MHJYJCPZTDJIOT-UHFFFAOYSA-N 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
JAGZUIGGHGTFHO-UHFFFAOYSA-N Ethyl 3-phenylpropanoate Chemical compound CCOC(=O)CCC1=CC=CC=C1 JAGZUIGGHGTFHO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
150000001993 dienes Chemical class 0.000 description 3
238000004821 distillation Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
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
101100456896 Drosophila melanogaster metl gene Proteins 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
NPZXJVJAHYWLJR-UHFFFAOYSA-N ethyl 2-acetyloxy-3-phenylpropanoate Chemical compound CCOC(=O)C(OC(C)=O)CC1=CC=CC=C1 NPZXJVJAHYWLJR-UHFFFAOYSA-N 0.000 description 2
HNOFMAVEDATAJR-UHFFFAOYSA-N ethyl 3-acetyloxy-3-phenylpropanoate Chemical compound CCOC(=O)CC(OC(C)=O)C1=CC=CC=C1 HNOFMAVEDATAJR-UHFFFAOYSA-N 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
150000002736 metal compounds Chemical class 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003283 rhodium Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
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 description 1
NWCHELUCVWSRRS-SECBINFHSA-N (2r)-2-hydroxy-2-phenylpropanoic acid Chemical compound OC(=O)[C@@](O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-SECBINFHSA-N 0.000 description 1
UGRSNCNEIIUJEA-UHFFFAOYSA-N (3-chlorophenyl)-[2-[(3-chlorophenyl)-[(2-methoxyphenyl)methyl]phosphanyl]ethyl]-[(2-methoxyphenyl)methyl]phosphane (4-chlorophenyl)-[2-[(4-chlorophenyl)-[(2-methoxyphenyl)methyl]phosphanyl]ethyl]-[(2-methoxyphenyl)methyl]phosphane (2-methoxyphenyl)methyl-[2-[(2-methoxyphenyl)methyl-(4-methylphenyl)phosphanyl]ethyl]-(4-methylphenyl)phosphane Chemical compound C(C=1C(=CC=CC1)OC)P(CCP(C1=CC(=CC=C1)Cl)CC=1C(=CC=CC1)OC)C1=CC(=CC=C1)Cl.C(C=1C(=CC=CC1)OC)P(CCP(C1=CC=C(C=C1)Cl)CC=1C(=CC=CC1)OC)C1=CC=C(C=C1)Cl.C(C=1C(=CC=CC1)OC)P(CCP(C1=CC=C(C=C1)C)CC=1C(=CC=CC1)OC)C1=CC=C(C=C1)C UGRSNCNEIIUJEA-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
239000004912 1,5-cyclooctadiene Substances 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000012018 catalyst precursor Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000000460 chlorine Chemical group 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
UMSUVRQADXVIDD-UHFFFAOYSA-N ethyl 2-acetyloxyprop-2-enoate Chemical class CCOC(=O)C(=C)OC(C)=O UMSUVRQADXVIDD-UHFFFAOYSA-N 0.000 description 1
CLRHEGMAWYPMJF-UHFFFAOYSA-N ethyl 2-oxo-3-phenylpropanoate Chemical compound CCOC(=O)C(=O)CC1=CC=CC=C1 CLRHEGMAWYPMJF-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000007701 flash-distillation Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
NGJIJGCJRNAGHK-UHFFFAOYSA-N methyl 2-acetyloxyprop-2-enoate Chemical class COC(=O)C(=C)OC(C)=O NGJIJGCJRNAGHK-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003284 rhodium compounds Chemical class 0.000 description 1
YWFDDXXMOPZFFM-UHFFFAOYSA-H rhodium(3+);trisulfate Chemical compound [Rh+3].[Rh+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YWFDDXXMOPZFFM-UHFFFAOYSA-H 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
WMUVAMXULTVKIW-UHFFFAOYSA-K tribromorhodium;hydrate Chemical compound O.Br[Rh](Br)Br WMUVAMXULTVKIW-UHFFFAOYSA-K 0.000 description 1
HSSMNYDDDSNUKH-UHFFFAOYSA-K trichlororhodium;hydrate Chemical compound O.Cl[Rh](Cl)Cl HSSMNYDDDSNUKH-UHFFFAOYSA-K 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH1070576A 1975-08-25 1976-08-24 Process for the preparation of enantiomorphs of acyloxypropionic acid derivatives with high optical purity CH624088A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US60709075A	1975-08-25	1975-08-25

Publications (1)

Publication Number	Publication Date
CH624088A5 true CH624088A5 (en)	1981-07-15

Family

ID=24430767

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1070576A CH624088A5 (en)	1975-08-25	1976-08-24	Process for the preparation of enantiomorphs of acyloxypropionic acid derivatives with high optical purity

Country Status (10)

Country	Link
JP (1)	JPS5850207B2 (fr)
AU (1)	AU499782B2 (fr)
BE (1)	BE845454A (fr)
BR (1)	BR7605568A (fr)
CA (1)	CA1086771A (fr)
CH (1)	CH624088A5 (fr)
DE (1)	DE2638070A1 (fr)
FR (1)	FR2322126A1 (fr)
GB (1)	GB1501558A (fr)
NL (1)	NL7609340A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9823716D0 (en)	1998-10-29	1998-12-23	Isis Innovation	Diphosphines

1976
- 1976-08-23 NL NL7609340A patent/NL7609340A/xx not_active Application Discontinuation
- 1976-08-24 CA CA259,754A patent/CA1086771A/fr not_active Expired
- 1976-08-24 FR FR7625642A patent/FR2322126A1/fr active Granted
- 1976-08-24 DE DE19762638070 patent/DE2638070A1/de not_active Ceased
- 1976-08-24 BR BR7605568A patent/BR7605568A/pt unknown
- 1976-08-24 BE BE170021A patent/BE845454A/fr not_active IP Right Cessation
- 1976-08-24 JP JP10027876A patent/JPS5850207B2/ja not_active Expired
- 1976-08-24 CH CH1070576A patent/CH624088A5/de not_active IP Right Cessation
- 1976-08-24 GB GB3512576A patent/GB1501558A/en not_active Expired
- 1976-08-24 AU AU17094/76A patent/AU499782B2/en not_active Expired

Also Published As

Publication number	Publication date
AU1709476A (en)	1978-03-02
FR2322126B1 (fr)	1980-05-16
FR2322126A1 (fr)	1977-03-25
CA1086771A (fr)	1980-09-30
JPS5227716A (en)	1977-03-02
BE845454A (fr)	1977-02-24
JPS5850207B2 (ja)	1983-11-09
NL7609340A (nl)	1977-03-01
AU499782B2 (en)	1979-05-03
BR7605568A (pt)	1977-08-09
DE2638070A1 (de)	1977-03-10
GB1501558A (en)	1978-02-15

Legal Events

Date	Code	Title	Description
1996-09-13	PL	Patent ceased

Publication	Publication Date	Title
DE2463010C2 (de)	1982-11-25	Optisch aktive Katalysatoren und deren Verwendung
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EP0564406B1 (fr)	1999-05-06	Ferrocenyldiphosphine comme ligandes de catalyseurs homogènes
EP0104375A1 (fr)	1984-04-04	Dérivés biphényliques contenant du phosphore et leur utilisation pour l'hydrogénation asymétrique et la migration énantiosélective d'hydrogène
DE2161200A1 (de)	1972-06-22	Neue zweibindige Liganden, ihre Herstellung und Verwendung
DE69114986T2 (de)	1996-08-01	Eine Phosphino-Binapthyl-Verbindung und Übergangsmetall-Komplexe davon.
EP0138141B1 (fr)	1988-02-24	Procédé pour l'hydrogénation sélective de doubles liaisons C-C en présence de groupes réductibles, contenant de l'azote
DE3874627T2 (de)	1993-03-11	Herstellungsverfahren eines optisch aktiven alkohols.
DE2538364B2 (de)	1978-02-23	Verfahren zur herstellung von butandiolen
EP0924182B1 (fr)	2003-07-02	Procédé pour la préparation d' aldéhydes
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DE2833538C2 (de)	1984-09-20	Verfahren zur Herstellung von &alpha;-methylverzweigten Aldehyden
DE2643205A1 (de)	1978-03-30	Verfahren zur herstellung von alpha-formylpropionsaeurealkylestern
DE19964298C2 (de)	2003-01-23	Verfahren zur Herstellung von substituierten Arylhalophosphinen
DE69004575T2 (de)	1994-05-19	Verbesserung bei der herstellung von chiralen katalysatoren auf basis von ruthenium- und phosphorkomplexen.
DE3148098C2 (fr)	1991-05-16
DE2312924A1 (de)	1973-09-27	Verfahren zur asymmetrischen reduktion von ketonen unter bildung optisch aktiver alkohole
DE69616913T2 (de)	2002-06-27	Verfahren zur Herstellung von 3,7-Dimethyl-5,7-octadien-1-ol oder Rosenoxid
DE2141186B2 (de)	1980-05-29	Verfahren zur Herstellung primärer oder sekundärer, ungesättigter Cg u. Cn - Alkohole
CH624088A5 (en)	1981-07-15	Process for the preparation of enantiomorphs of acyloxypropionic acid derivatives with high optical purity
DE69318666T2 (de)	1998-09-10	Verfahren zur Herstellung von optisch aktiven gamma-Hydroxyketonen
DE2123063C3 (de)	1978-07-20	Katalytische asymmetrische Hydrierung
EP0512415B1 (fr)	1997-08-06	Procédé pour la préparation enantiosélective des dérivés de 2(R) benzyl succinamide
DE602005005354T2 (de)	2009-03-26	Verfahren zur herstellung von 1,4-dialkyl-2,3-diol-1,4-butandion
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