JPS5929045B2 - 光学活性物質の製法 - Google Patents
光学活性物質の製法Info
- Publication number
- JPS5929045B2 JPS5929045B2 JP49040466A JP4046674A JPS5929045B2 JP S5929045 B2 JPS5929045 B2 JP S5929045B2 JP 49040466 A JP49040466 A JP 49040466A JP 4046674 A JP4046674 A JP 4046674A JP S5929045 B2 JPS5929045 B2 JP S5929045B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- optically active
- general formula
- group
- alkyl group
- 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.)
- Expired
Links
- 239000013543 active substance Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 150000002466 imines Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 4
- 229910018509 Al—N Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 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
- 238000006243 chemical reaction Methods 0.000 description 11
- 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 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- -1 lithium hydrides Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 150000003335 secondary amines Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910010084 LiAlH4 Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 2
- 238000011914 asymmetric synthesis Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- 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
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 229910000086 alane Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000091 aluminium hydride Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 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
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer 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
- ZKALVNREMFLWAN-UHFFFAOYSA-N n-(4-methylpentan-2-ylidene)hydroxylamine Chemical compound CC(C)CC(C)=NO ZKALVNREMFLWAN-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000002994 raw material Substances 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
- 238000000926 separation method Methods 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-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)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| 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 |
| IT22954 | 1973-04-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5076002A JPS5076002A (cs) | 1975-06-21 |
| JPS5929045B2 true JPS5929045B2 (ja) | 1984-07-18 |
Family
ID=11202251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49040466A Expired JPS5929045B2 (ja) | 1973-04-13 | 1974-04-12 | 光学活性物質の製法 |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5929045B2 (cs) |
| BE (1) | BE813718A (cs) |
| CA (1) | CA1021801A (cs) |
| CH (1) | CH606032A5 (cs) |
| CS (1) | CS203074B2 (cs) |
| DD (1) | DD113740A5 (cs) |
| DK (1) | DK137922B (cs) |
| FR (1) | FR2225397B1 (cs) |
| GB (1) | GB1460781A (cs) |
| HU (1) | HU176607B (cs) |
| IT (1) | IT987071B (cs) |
| LU (1) | LU69850A1 (cs) |
| NL (1) | NL7404845A (cs) |
| NO (1) | NO142864C (cs) |
| SE (1) | SE419550B (cs) |
| YU (1) | YU96574A (cs) |
| ZA (1) | ZA742324B (cs) |
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 |
| WO2006079819A2 (en) * | 2005-01-27 | 2006-08-03 | 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 FR FR7412543A patent/FR2225397B1/fr not_active Expired
- 1974-04-10 ZA ZA00742324A patent/ZA742324B/xx unknown
- 1974-04-10 DK DK202374AA patent/DK137922B/da not_active IP Right Cessation
- 1974-04-10 SE SE7404949A patent/SE419550B/xx not_active IP Right Cessation
- 1974-04-11 DD DD177852A patent/DD113740A5/xx unknown
- 1974-04-11 CA CA197,532A patent/CA1021801A/en not_active Expired
- 1974-04-12 LU LU69850A patent/LU69850A1/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 BE BE143208A patent/BE813718A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2225397B1 (cs) | 1976-06-25 |
| JPS5076002A (cs) | 1975-06-21 |
| BE813718A (fr) | 1974-07-31 |
| SE419550B (sv) | 1981-08-10 |
| DD113740A5 (cs) | 1975-06-20 |
| NO142864C (no) | 1980-11-05 |
| NO142864B (no) | 1980-07-28 |
| CS203074B2 (en) | 1981-02-27 |
| DE2416396B2 (de) | 1977-02-17 |
| YU96574A (en) | 1982-05-31 |
| GB1460781A (en) | 1977-01-06 |
| AU6753874A (en) | 1975-10-09 |
| CA1021801A (en) | 1977-11-29 |
| NL7404845A (cs) | 1974-10-15 |
| DE2416396A1 (de) | 1974-10-31 |
| FR2225397A1 (cs) | 1974-11-08 |
| DK137922B (da) | 1978-06-05 |
| NO741246L (no) | 1974-10-15 |
| CH606032A5 (cs) | 1978-10-13 |
| HU176607B (en) | 1981-03-28 |
| DK137922C (cs) | 1978-10-30 |
| IT987071B (it) | 1975-02-20 |
| ZA742324B (en) | 1975-04-30 |
| LU69850A1 (cs) | 1974-07-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE452608B (sv) | Forfarande for uppspjelkning av en racemisk modifikation av beta-adrenergiska aryl- eller hetaryloxipropanolaminer | |
| EP0441160A1 (en) | Process for preparing levo and dextro fenfluramine | |
| JP2792046B2 (ja) | 光学活性なアミン−ホウ素系化合物、それを有効成分とする不斉還元剤ならびにそれを用いる光学活性化合物の製造方法 | |
| US5200561A (en) | Process for producing optically active amines | |
| JPS5929045B2 (ja) | 光学活性物質の製法 | |
| US5145998A (en) | Method for producing optically active amines | |
| CN116396189B (zh) | 一种(s)-(+)-1-茚满基异氰酸酯的制备方法 | |
| US4053521A (en) | Asymmetrical hydrogenation by means of optically active aluminum hydride derivatives | |
| US2582292A (en) | Preparation of benzal-imino compounds | |
| CN102126961B (zh) | R-1-（4-甲氧基苯基）-n-苄基-2-丙胺制备方法 | |
| US5756790A (en) | Optically active cobalt (II) complexes and method for the preparation of optically active alcohols | |
| JPH0386873A (ja) | １，３―ジオキソランケトンの製法 | |
| EP3606908B1 (en) | Resolution of racemic beta-aminosulfone compounds | |
| US7816533B2 (en) | Asymmetric imine hydrogenation processes | |
| JPH0720917B2 (ja) | 含窒素ペルフルオロカルボン酸の光学活性体及びその製造方法 | |
| US5688985A (en) | Process for producing keto nitrile derivative | |
| US7465830B2 (en) | Method of preparing pseudonorephedrine | |
| CA2273012A1 (fr) | Procede de dedoublement de composes 1-amino-alcan-2-ol | |
| JP2838529B2 (ja) | 新規な光学活性化合物 | |
| JPH0827072A (ja) | ２−メチル−１，２−プロパンジアミンの製造方法 | |
| JPS6399041A (ja) | 光学活性アミン類の製造方法 | |
| CN113117744A (zh) | 联二萘骨架衍生的手性含糖氨基硫脲催化剂及其制备方法、用途 | |
| JPH08109190A (ja) | アミン類およびアルコール類の光学純度並びに立体配置決定に有効なオキサアザシクロホスファミド誘導体 | |
| JP2946678B2 (ja) | キラルなフェロセン誘導体 | |
| CN110803981A (zh) | 间叔丁基苯酚的合成方法 |