ZA200806473B - An efficient process to induce enantioselectivity in procarbonyl compounds - Google Patents
An efficient process to induce enantioselectivity in procarbonyl compounds Download PDFInfo
- Publication number
- ZA200806473B ZA200806473B ZA200806473A ZA200806473A ZA200806473B ZA 200806473 B ZA200806473 B ZA 200806473B ZA 200806473 A ZA200806473 A ZA 200806473A ZA 200806473 A ZA200806473 A ZA 200806473A ZA 200806473 B ZA200806473 B ZA 200806473B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- metal
- chiral
- reagent
- base
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 46
- 150000001875 compounds Chemical class 0.000 title claims description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims description 34
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 28
- 125000002524 organometallic group Chemical group 0.000 claims description 25
- 239000000654 additive Substances 0.000 claims description 24
- 230000000996 additive effect Effects 0.000 claims description 24
- 150000004696 coordination complex Chemical class 0.000 claims description 23
- 229910001507 metal halide Inorganic materials 0.000 claims description 22
- 150000005309 metal halides Chemical class 0.000 claims description 22
- 125000001475 halogen functional group Chemical group 0.000 claims description 21
- 239000011701 zinc Substances 0.000 claims description 21
- 229910052725 zinc Inorganic materials 0.000 claims description 20
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000001345 alkine derivatives Chemical group 0.000 claims description 11
- -1 copper halides Chemical class 0.000 claims description 11
- 229910052987 metal hydride Inorganic materials 0.000 claims description 11
- 150000004681 metal hydrides Chemical group 0.000 claims description 11
- 230000002152 alkylating effect Effects 0.000 claims description 10
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 8
- 150000004703 alkoxides Chemical class 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 239000007818 Grignard reagent Substances 0.000 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 150000004795 grignard reagents Chemical group 0.000 claims description 6
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 6
- 150000004692 metal hydroxides Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000001414 amino alcohols Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 235000016804 zinc Nutrition 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 4
- 229960002179 ephedrine Drugs 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 4
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 4
- NOKSRMDODJGCPZ-UHFFFAOYSA-N 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C(F)(F)F NOKSRMDODJGCPZ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 3
- OSXAEVZRGCKZLH-UHFFFAOYSA-M magnesium;ethynylcyclopropane;chloride Chemical compound [Mg+2].[Cl-].[C-]#CC1CC1 OSXAEVZRGCKZLH-UHFFFAOYSA-M 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- QILVTBCJVNFIDP-NTISSMGPSA-N (1r)-2-[2-(4-aminophenyl)ethylamino]-1-phenylethanol;hydrochloride Chemical compound Cl.C1=CC(N)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 QILVTBCJVNFIDP-NTISSMGPSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000004792 aryl magnesium halides Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- NPTDXPDGUHAFKC-UHFFFAOYSA-N ethynylcyclopropane Chemical group C#CC1CC1 NPTDXPDGUHAFKC-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- 229940102001 zinc bromide Drugs 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN262CH2008 | 2008-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200806473B true ZA200806473B (en) | 2009-04-29 |
Family
ID=40913373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200806473A ZA200806473B (en) | 2008-01-31 | 2008-07-24 | An efficient process to induce enantioselectivity in procarbonyl compounds |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9156756B2 (zh) |
| EP (1) | EP2235023B1 (zh) |
| CN (1) | CN101497573B (zh) |
| CY (1) | CY1115209T1 (zh) |
| DK (1) | DK2235023T3 (zh) |
| ES (1) | ES2449754T3 (zh) |
| PL (1) | PL2235023T3 (zh) |
| SI (1) | SI2235023T1 (zh) |
| WO (1) | WO2009095931A2 (zh) |
| ZA (1) | ZA200806473B (zh) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9073817B2 (en) * | 2008-01-31 | 2015-07-07 | Laurus Labs Private Limited | Efficient process to induce enantioselectivity in procarbonyl compounds |
| WO2011000532A2 (de) | 2009-07-03 | 2011-01-06 | Archimica Gmbh | Verfahren zur enantioselektiven addition von organometallischen kohlenstoffnukleophilen an trifluormethylketone und verwendung des verfahrens in der synthese von hiv reverse transcriptase inhibitoren |
| CN102372533B (zh) * | 2011-11-01 | 2014-08-13 | 浙江新华制药有限公司 | 酒石酸衍生物催化端炔锌试剂对含氟烷基芳酮的不对称加成方法 |
| CN102617370B (zh) * | 2012-03-05 | 2014-06-04 | 浙江江北药业有限公司 | (S)-5-氯-α-(环丙乙炔基)-2-(((4-甲氧基苯基)甲基)氨基)-α-(三氟甲基)苯甲醇的制备方法 |
| CN103833560B (zh) * | 2013-03-25 | 2016-05-25 | 安徽贝克联合制药有限公司 | (S)-5-氯-α-环丙炔基-2-氨基-α-三氟甲基苯甲醇的制备方法 |
| CN105330554B (zh) | 2015-02-15 | 2017-07-11 | 上海迪赛诺药业股份有限公司 | 手性环丙基乙炔基叔醇类化合物的合成方法 |
| CN111548317A (zh) * | 2020-04-28 | 2020-08-18 | 苏州纪元康生物科技有限公司 | 一种依法韦伦合成方法及制备其中间体方法 |
| CN113968791A (zh) * | 2021-11-18 | 2022-01-25 | 盐城迪赛诺制药有限公司 | 一种依非韦伦关键中间体的制备方法 |
| CN115010682A (zh) * | 2022-06-24 | 2022-09-06 | 盐城迪赛诺制药有限公司 | 依非韦伦关键中间体酸化过程无机酸替代有机酸的方法 |
| CN115073310A (zh) * | 2022-07-05 | 2022-09-20 | 盐城迪赛诺制药有限公司 | 一种降低依非韦伦关键中间体母液中特定杂质的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5519021A (en) * | 1992-08-07 | 1996-05-21 | Merck & Co., Inc. | Benzoxazinones as inhibitors of HIV reverse transcriptase |
| US5633405A (en) * | 1995-05-25 | 1997-05-27 | Merck & Co., Inc. | Asymmetric synthesis of (-)-6-chloro-4-cyclopropyl-ethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxanzin-2-one |
| US6015926A (en) * | 1997-05-16 | 2000-01-18 | Merck & Co., Inc. | Efficient enantioselective addition reaction using an organozinc reagent |
| DE19812480A1 (de) * | 1998-03-21 | 1999-09-23 | E B S Gmbh | Tintenstrahldrucker für die Beschriftung von Waren |
| US6586644B2 (en) * | 2001-10-05 | 2003-07-01 | Erick M. Carreira | Process for producing optically active propargyl alcohols |
| EP1614672B1 (en) | 2003-04-04 | 2010-09-22 | Shanghai Institute Of Organic Chemistry, Chinese Academy Of Sciences | An amino alcohol ligand and its use in preparation of chiral proparglic tertiary alkohols and tertiary amines via enantioselective additon reaction |
| WO2011000532A2 (de) | 2009-07-03 | 2011-01-06 | Archimica Gmbh | Verfahren zur enantioselektiven addition von organometallischen kohlenstoffnukleophilen an trifluormethylketone und verwendung des verfahrens in der synthese von hiv reverse transcriptase inhibitoren |
-
2008
- 2008-07-24 ZA ZA200806473A patent/ZA200806473B/en unknown
- 2008-07-30 EP EP08808147.6A patent/EP2235023B1/en active Active
- 2008-07-30 DK DK08808147.6T patent/DK2235023T3/en active
- 2008-07-30 WO PCT/IN2008/000476 patent/WO2009095931A2/en active Application Filing
- 2008-07-30 US US12/667,985 patent/US9156756B2/en active Active
- 2008-07-30 ES ES08808147.6T patent/ES2449754T3/es active Active
- 2008-07-30 SI SI200831165T patent/SI2235023T1/sl unknown
- 2008-07-30 PL PL08808147T patent/PL2235023T3/pl unknown
- 2008-10-23 CN CN2008101717247A patent/CN101497573B/zh not_active Expired - Fee Related
-
2014
- 2014-03-11 CY CY20141100196T patent/CY1115209T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US9156756B2 (en) | 2015-10-13 |
| CY1115209T1 (el) | 2017-01-04 |
| WO2009095931A2 (en) | 2009-08-06 |
| US20100286408A1 (en) | 2010-11-11 |
| SI2235023T1 (sl) | 2014-04-30 |
| EP2235023A4 (en) | 2011-09-07 |
| EP2235023A2 (en) | 2010-10-06 |
| WO2009095931A3 (en) | 2010-09-30 |
| EP2235023B1 (en) | 2013-12-11 |
| ES2449754T3 (es) | 2014-03-21 |
| DK2235023T3 (en) | 2014-03-10 |
| CN101497573A (zh) | 2009-08-05 |
| PL2235023T3 (pl) | 2014-07-31 |
| CN101497573B (zh) | 2013-09-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200806473B (en) | An efficient process to induce enantioselectivity in procarbonyl compounds | |
| JP2008526822A (ja) | 塩基安定性イオン液体 | |
| CN105392791B (zh) | 制备氯代酰联苯胺和联苯胺的改进方法 | |
| JP5623389B2 (ja) | 置換ビフェニルアニリド類を調製する方法 | |
| CN107930696A (zh) | 三甲茂稀土配合物在催化亚胺和硼烷的硼氢化反应中的应用 | |
| US20040106818A1 (en) | Process for the preparation of cyclohexanol derivatives | |
| EP1582524A1 (en) | Method of preparing organomagnesium compounds | |
| JPH08253486A (ja) | ペンタフルオロフエニル化合物を製造するための方法 | |
| JP2001104795A (ja) | ルテニウム触媒組成物 | |
| CN104529796A (zh) | 一种基于受阻路易斯酸碱对的催化合成应用 | |
| CA3186051A1 (en) | Method for producing optically active compound | |
| US6187966B1 (en) | Process for preparing optically active alcoholic compounds | |
| KR100521062B1 (ko) | (3-알콕시페닐)마그네슘클로라이드의제조방법및당해클로라이드를사용한알콜제조방법 | |
| US10428098B2 (en) | Processes for preparing and using ruthenium and osmium complexes | |
| US9382280B2 (en) | Diamine compound and metal complexes, and method for producing optically active compounds | |
| WO2009137294A1 (en) | Processes for synthesizing 1-(2-ethylbutyl) cyclohexane carbonitrile | |
| TWI797784B (zh) | 環戊二烯的選擇性烷基化 | |
| CN101466662B (zh) | 氟代胺的制备方法 | |
| JP5889030B2 (ja) | 多環式芳香族化合物の製造方法 | |
| CN101837303A (zh) | 一种新型镍催化剂及其制备方法和应用 | |
| JP3751713B2 (ja) | トリアリールボランホスフィン錯体の製造法 | |
| CN102643163A (zh) | 格氏反应制备叔醇的方法 | |
| JP2014024777A (ja) | ハロゲン原子を有する多環式芳香族化合物の製造方法 | |
| KR101654787B1 (ko) | 팔라듐 케토이미네이트 착화합물을 함유하는 촉매 조성물 및 이를 이용한 크로스커플링 화합물의 제조 방법 | |
| JP5837843B2 (ja) | ハロゲン原子を有する多環式芳香族化合物の製造方法 |