CS203074B2 - Method for the asymmetric reduction of prochiral or racemic substrates - Google Patents
Method for the asymmetric reduction of prochiral or racemic substrates Download PDFInfo
- Publication number
- CS203074B2 CS203074B2 CS742668A CS266874A CS203074B2 CS 203074 B2 CS203074 B2 CS 203074B2 CS 742668 A CS742668 A CS 742668A CS 266874 A CS266874 A CS 266874A CS 203074 B2 CS203074 B2 CS 203074B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- optically active
- bond
- prochiral
- reduction
- yield
- Prior art date
Links
- 230000009467 reduction Effects 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims abstract description 8
- 239000000758 substrate Substances 0.000 title claims description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910018509 Al—N Inorganic materials 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000002466 imines Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052782 aluminium Inorganic materials 0.000 abstract description 3
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 abstract description 2
- CWKYHZMWPLSOFA-UHFFFAOYSA-N 3-methyl-1-phenyl-2,5-dihydrophosphole Chemical compound C1C(C)=CCP1C1=CC=CC=C1 CWKYHZMWPLSOFA-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 229910000086 alane Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- ZFAGOADKDXXTSV-UHFFFAOYSA-N 3-methylpentan-2-amine Chemical compound CCC(C)C(C)N ZFAGOADKDXXTSV-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 230000003287 optical effect Effects 0.000 description 21
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- SASNBVQSOZSTPD-UHFFFAOYSA-N n-methylphenethylamine Chemical compound CNCCC1=CC=CC=C1 SASNBVQSOZSTPD-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 alkoxy hydrides Chemical class 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- SPRIOUNJHPCKPV-UHFFFAOYSA-N hydridoaluminium Chemical compound [AlH] SPRIOUNJHPCKPV-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical group 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
- MDFWXZBEVCOVIO-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptan-3-amine Chemical compound C1CC2(C)C(N)CC1C2(C)C MDFWXZBEVCOVIO-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000091 aluminium hydride Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000003798 microbiological reaction Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- QKYWADPCTHTJHQ-UHFFFAOYSA-N n,2-dimethylpropan-1-amine Chemical compound CNCC(C)C QKYWADPCTHTJHQ-UHFFFAOYSA-N 0.000 description 1
- MYWUZJCMWCOHBA-UHFFFAOYSA-N n-methyl-1-phenylpropan-2-amine Chemical compound CNC(C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-UHFFFAOYSA-N 0.000 description 1
- HRGRUCGUHMULFW-UHFFFAOYSA-N n-undecan-6-ylidenehydroxylamine Chemical compound CCCCCC(=NO)CCCCC HRGRUCGUHMULFW-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/509—Preparation; Separation; Purification; Stabilisation by reduction of pentavalent phosphorus derivatives, e.g. -P=X with X = O, S, Se or -P-Hal2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22954/73A IT987071B (it) | 1973-04-13 | 1973-04-13 | Idrogenazione asimmetrica a mez zo di derivati otticamente atti vi dell idroro di alluminio |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203074B2 true CS203074B2 (en) | 1981-02-27 |
Family
ID=11202251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS742668A CS203074B2 (en) | 1973-04-13 | 1974-04-12 | Method for the asymmetric reduction of prochiral or racemic substrates |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5929045B2 (it) |
| BE (1) | BE813718A (it) |
| CA (1) | CA1021801A (it) |
| CH (1) | CH606032A5 (it) |
| CS (1) | CS203074B2 (it) |
| DD (1) | DD113740A5 (it) |
| DK (1) | DK137922B (it) |
| FR (1) | FR2225397B1 (it) |
| GB (1) | GB1460781A (it) |
| HU (1) | HU176607B (it) |
| IT (1) | IT987071B (it) |
| LU (1) | LU69850A1 (it) |
| NL (1) | NL7404845A (it) |
| NO (1) | NO142864C (it) |
| SE (1) | SE419550B (it) |
| YU (1) | YU96574A (it) |
| ZA (1) | ZA742324B (it) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2714721A1 (de) * | 1976-05-17 | 1977-12-01 | Texas Alkyls Inc | Reduktion von triphenylphosphinoxid zu triphenylphosphin |
| US5189208A (en) * | 1991-07-01 | 1993-02-23 | Ethyl Corporation | Ibuprofen resolution |
| EP1846350A2 (en) * | 2005-01-27 | 2007-10-24 | University of Nottingham | Improved method for the preparation of enantiomerically enriched secondary alcohols by the addition of organoaluminium reagents to carbonyl compounds |
-
1973
- 1973-04-13 IT IT22954/73A patent/IT987071B/it active
-
1974
- 1974-04-04 NO NO741246A patent/NO142864C/no unknown
- 1974-04-08 YU YU00965/74A patent/YU96574A/xx unknown
- 1974-04-08 CH CH487074A patent/CH606032A5/xx not_active IP Right Cessation
- 1974-04-09 NL NL7404845A patent/NL7404845A/xx active Search and Examination
- 1974-04-09 GB GB1578174A patent/GB1460781A/en not_active Expired
- 1974-04-10 ZA ZA00742324A patent/ZA742324B/xx unknown
- 1974-04-10 SE SE7404949A patent/SE419550B/xx not_active IP Right Cessation
- 1974-04-10 FR FR7412543A patent/FR2225397B1/fr not_active Expired
- 1974-04-10 DK DK202374AA patent/DK137922B/da not_active IP Right Cessation
- 1974-04-11 CA CA197,532A patent/CA1021801A/en not_active Expired
- 1974-04-11 DD DD177852A patent/DD113740A5/xx unknown
- 1974-04-12 JP JP49040466A patent/JPS5929045B2/ja not_active Expired
- 1974-04-12 HU HU74SA2625A patent/HU176607B/hu unknown
- 1974-04-12 CS CS742668A patent/CS203074B2/cs unknown
- 1974-04-12 LU LU69850A patent/LU69850A1/xx unknown
- 1974-04-12 BE BE143208A patent/BE813718A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA742324B (en) | 1975-04-30 |
| JPS5929045B2 (ja) | 1984-07-18 |
| FR2225397A1 (it) | 1974-11-08 |
| DE2416396A1 (de) | 1974-10-31 |
| NO741246L (no) | 1974-10-15 |
| NO142864B (no) | 1980-07-28 |
| CH606032A5 (it) | 1978-10-13 |
| YU96574A (en) | 1982-05-31 |
| IT987071B (it) | 1975-02-20 |
| LU69850A1 (it) | 1974-07-18 |
| DD113740A5 (it) | 1975-06-20 |
| DK137922B (da) | 1978-06-05 |
| HU176607B (en) | 1981-03-28 |
| NL7404845A (it) | 1974-10-15 |
| CA1021801A (en) | 1977-11-29 |
| NO142864C (no) | 1980-11-05 |
| AU6753874A (en) | 1975-10-09 |
| JPS5076002A (it) | 1975-06-21 |
| DK137922C (it) | 1978-10-30 |
| DE2416396B2 (de) | 1977-02-17 |
| FR2225397B1 (it) | 1976-06-25 |
| BE813718A (fr) | 1974-07-31 |
| GB1460781A (en) | 1977-01-06 |
| SE419550B (sv) | 1981-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0441160B1 (en) | Process for preparing levo and dextro fenfluramine | |
| HU193183B (en) | Process for separating optical isomeres of optically active phenoxy-propanol-amine derivatives | |
| CA1269997A (en) | Racemization process | |
| WO1991001957A1 (en) | Resolution of racemic mixtures | |
| EP0485069B1 (en) | Process for producing optically active amines | |
| KR960000758B1 (ko) | 광학적 활성 히드록시벤질아민 유도체 및 그의 제조방법 | |
| CS203074B2 (en) | Method for the asymmetric reduction of prochiral or racemic substrates | |
| EP0237305B1 (en) | A method for producing optically active amines | |
| EP0169300B1 (en) | Process for preparation of alpha-alkyl amino acids | |
| US4053521A (en) | Asymmetrical hydrogenation by means of optically active aluminum hydride derivatives | |
| FR3021050A1 (fr) | Procede de preparation d'acide boriniques | |
| EP0322236B1 (en) | Catalytic process for preparing optically active threonine | |
| EP0169614B1 (en) | Process for the preparation of l-carnitine | |
| US4411840A (en) | Process for the resolution of the racemate S-(carboxymethyl)-(RS)-cysteine (B) | |
| JP2679248B2 (ja) | 光学活性アミン類の製造方法 | |
| JPH0645577B2 (ja) | 光学活性アミン類の製造方法 | |
| US4713463A (en) | Synthesis of n-epoxypropyl lactams | |
| JP2831776B2 (ja) | 異性体分離法 | |
| JP2005306804A (ja) | 光学活性３−キヌクリジノールの製造方法 | |
| JPS60149593A (ja) | アミンボラン類の製造方法 | |
| JPS6379854A (ja) | 含フツ素有機化合物 | |
| JP2946678B2 (ja) | キラルなフェロセン誘導体 | |
| US20010005762A1 (en) | Methods for producing and separating erythro- and threo-2-hydroxy-3-nitrobutanoic acid compounds | |
| JPS6033380B2 (ja) | 光学活性アミノアルコ−ルの製法 | |
| JP2000512643A (ja) | 光学的に活性な１―フェニルエチルアミン類の製造方法 |