ATE520678T1 - Asymmetrische hydrierung von alkenen mit chiralem iridiumkomplex - Google Patents
Asymmetrische hydrierung von alkenen mit chiralem iridiumkomplexInfo
- Publication number
- ATE520678T1 ATE520678T1 AT05820633T AT05820633T ATE520678T1 AT E520678 T1 ATE520678 T1 AT E520678T1 AT 05820633 T AT05820633 T AT 05820633T AT 05820633 T AT05820633 T AT 05820633T AT E520678 T1 ATE520678 T1 AT E520678T1
- Authority
- AT
- Austria
- Prior art keywords
- alkenes
- iridium complex
- asymmetric hydrogenation
- chiral iridium
- hydrogenation
- Prior art date
Links
- 150000001336 alkenes Chemical class 0.000 title 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 title 1
- 229910052741 iridium Inorganic materials 0.000 title 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title 1
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 230000000707 stereoselective effect Effects 0.000 abstract 2
- 229930003802 tocotrienol Natural products 0.000 abstract 2
- 239000011731 tocotrienol Substances 0.000 abstract 2
- 229940068778 tocotrienols Drugs 0.000 abstract 2
- 235000019148 tocotrienols Nutrition 0.000 abstract 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000000284 extract Substances 0.000 abstract 1
- 239000010773 plant oil Substances 0.000 abstract 1
- 150000003505 terpenes Chemical class 0.000 abstract 1
- 150000003610 tocomonoenols Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04030432 | 2004-12-22 | ||
| PCT/EP2005/013694 WO2006066863A1 (en) | 2004-12-22 | 2005-12-20 | Asymmetric hydrogenation of alkennes using chiral iridium complexes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE520678T1 true ATE520678T1 (de) | 2011-09-15 |
Family
ID=35994658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT05820633T ATE520678T1 (de) | 2004-12-22 | 2005-12-20 | Asymmetrische hydrierung von alkenen mit chiralem iridiumkomplex |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8426617B2 (de) |
| EP (1) | EP1828159B1 (de) |
| JP (1) | JP5090926B2 (de) |
| KR (1) | KR101342722B1 (de) |
| CN (1) | CN101087774B (de) |
| AT (1) | ATE520678T1 (de) |
| ES (1) | ES2371653T3 (de) |
| WO (1) | WO2006066863A1 (de) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101565366B (zh) * | 2008-04-25 | 2013-04-17 | 浙江九洲药业股份有限公司 | 铱络合物在不饱和羧酸不对称催化氢化中的应用 |
| GB2466629B (en) * | 2008-12-29 | 2011-08-17 | Schlumberger Holdings | Catalytic hydrogenation |
| WO2010125035A1 (de) * | 2009-04-30 | 2010-11-04 | Basf Se | Metallkomplex mit schwach koordinierendem gegenion als polymerisationskatalysator für isobuten oder ein isobuten-haltiges monomerengemisch |
| ES2608780T3 (es) | 2010-08-23 | 2017-04-17 | Novartis Ag | Nuevo proceso para la preparación de intermediarios útiles para la elaboración de inhibidores de NEP |
| EP2522647B1 (de) * | 2011-05-10 | 2014-04-30 | DSM IP Assets B.V. | Verfahren zum Trennen von chiralen Isomeren von Chromverbindungen und ihre Derivate und Vorläufer |
| EP2535323A1 (de) * | 2011-06-14 | 2012-12-19 | DSM IP Assets B.V. | Hydrierung von Ketonen mit mindestens einer Kohlenstoff-Doppelbindung in der gamma-,delta-Position |
| CN104520284B (zh) | 2012-08-10 | 2018-01-26 | 帝斯曼知识产权资产管理有限公司 | 具有含量降低的游离生育酚的经保护生育酚 |
| CN104520286B (zh) | 2012-08-10 | 2018-01-26 | 帝斯曼知识产权资产管理有限公司 | 颜色稳定性增加的生育酚 |
| WO2014096066A1 (en) * | 2012-12-18 | 2014-06-26 | Dsm Ip Assets B.V. | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from (r)-3,7-dimetyloct-6-enal |
| CN109970533B (zh) * | 2012-12-18 | 2022-06-14 | 帝斯曼知识产权资产管理有限公司 | 由(r)-6，10，14-三甲基十五碳-5-烯-2-酮制备的(6r，10r)-6，10，14-三甲基十五烷-2-酮 |
| EP2935188B1 (de) * | 2012-12-18 | 2018-08-01 | DSM IP Assets B.V. | Verwendung von mischungen aus e/z-isomeren zum erhalten von quantitativ spezifischen produkten durch kombinierte asymmetrische hydrierungen |
| JP6582324B2 (ja) | 2012-12-18 | 2019-10-02 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | ６，１０，１４−トリメチルペンタデカ−５，９，１３−トリエン−２−オンまたは６，１０，１４−トリメチルペンタデカ−５，９−ジエン−２−オンから調製した（６ｒ，１０ｒ）−６，１０，１４−トリメチルペンタデカン−２−オン |
| EP2935233B1 (de) * | 2012-12-18 | 2019-01-30 | DSM IP Assets B.V. | Verfahren zur asymmetrischen hydrierung von ketalen und acetalen |
| JP6481171B2 (ja) * | 2012-12-18 | 2019-03-13 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | ６，１０−ジメチルウンデカ−５−エン−２−オンまたは６，１０−ジメチルウンデカ−５，９−ジエン−２−オンから調製した（６ｒ，１０ｒ）−６，１０，１４−トリメチルペンタデカン−２−オン |
| CN104854072A (zh) * | 2012-12-18 | 2015-08-19 | 帝斯曼知识产权资产管理有限公司 | 由6,10-二甲基十一碳-3,5,9-三烯-2-酮制备的(6r,10r)-6,10,14-三甲基十五烷-2-酮 |
| MY171808A (en) * | 2012-12-18 | 2019-10-30 | Dsm Ip Assets Bv | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 3,7-dimetyloct-2-enal or 3,7-dimetylocta-2,6-dienal |
| ES2739229T3 (es) | 2012-12-18 | 2020-01-29 | Dsm Ip Assets Bv | Uso de mezclas de isómeros E/Z para obtener productos cuantitativamente específicos combinando hidrogenación asimétrica e isomerización |
| US10047019B2 (en) | 2012-12-18 | 2018-08-14 | Dsm Ip Assets B.V. | Efficient process of asymmetric hydrogenation of unsaturated ketones using additives |
| EP3016941B1 (de) | 2013-07-05 | 2017-03-22 | DSM IP Assets B.V. | Herstellung von chiralen 4-chromanonen unter verwendung von chiralen pyrrolidinen in gegenwart von harnstoffen oder thioharnstoffen |
| EP3016942B1 (de) | 2013-07-05 | 2017-03-01 | DSM IP Assets B.V. | Herstellung von chiralen 4-chromanonen unter verwendung von chiralen pyrrolidinen |
| EP2842951A1 (de) | 2013-08-30 | 2015-03-04 | DSM IP Assets B.V. | Bildung von Chromanen und Chromenen durch Verwendung von Silber(I)- oder Gold(I)-Salzen oder -Komplexen |
| JP6786761B2 (ja) | 2015-05-26 | 2020-11-18 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | Ｓｆｃによるキラル異性体の分離 |
| WO2018108606A1 (en) * | 2016-12-12 | 2018-06-21 | Dsm Ip Assets B.V. | Process for the manufacture of 6,10-dimethylundecan-2-one, isophytol, alpha-tocopherol (acetate) and further intermediates thereof |
| KR102819124B1 (ko) * | 2018-10-02 | 2025-06-12 | 주식회사 글라세움 | 탄소 이중결합 함유 화합물의 비대칭 수소첨가 반응용 촉매 |
| CN114790221B (zh) * | 2022-05-25 | 2024-07-12 | 西安交通大学 | 一种基于吲哚骨架的pcp钳形配体的合成及应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63152337A (ja) * | 1986-08-27 | 1988-06-24 | Takasago Corp | 光学活性アルコ−ルの製法 |
| EP0258967B2 (de) | 1986-08-27 | 1996-08-21 | Takasago Perfumery Co., Ltd. | Herstellungsverfahren von optisch aktiven Alkoholen |
| DE3813624A1 (de) * | 1988-04-22 | 1989-11-02 | Basf Ag | Verfahren zur herstellung von d-(alpha)-tocopherol aus natuerlichen vorprodukten |
| DE59009670D1 (de) | 1989-05-18 | 1995-10-26 | Hoffmann La Roche | Phosphorverbindungen. |
| JPH0474192A (ja) | 1990-07-12 | 1992-03-09 | Takasago Internatl Corp | ２，２′―ビス（ジシクロペンチルホスフィノ）―１，１′―ビナフチル及びこれれを配位子とする遷移金属錯体 |
| ATE142191T1 (de) * | 1992-04-16 | 1996-09-15 | Hoffmann La Roche | Verfahren zur herstellung von isoprenderivaten |
| DE19619013A1 (de) | 1996-05-10 | 1997-11-13 | Basf Ag | Verfahren zur Herstellung von Hexahydrofarnesylaceton aus 6,7-Dihydro-geraniol sowie neue Zwischenprodukte für dieses Verfahren |
| JPH10114767A (ja) | 1996-10-09 | 1998-05-06 | Sumitomo Chem Co Ltd | トコフェロール誘導体の製造法 |
| JPH10251248A (ja) | 1997-01-08 | 1998-09-22 | Sumitomo Chem Co Ltd | クロマン誘導体の製造法 |
| EP1095034A1 (de) * | 1998-07-06 | 2001-05-02 | Eastman Chemical Company | Darstellung von tocoferolen |
| US6410755B1 (en) | 1998-07-06 | 2002-06-25 | Dcv, Inc. | Method of vitamin production |
| JP3771070B2 (ja) | 1998-12-24 | 2006-04-26 | 高砂香料工業株式会社 | 軸不斉化合物の製造方法、その製造中間体、新規な軸不斉化合物を配位子とする遷移金属錯体、不斉水素化触媒及び不斉炭素−炭素結合形成触媒 |
| ATE294806T1 (de) | 2000-09-21 | 2005-05-15 | Solvias Ag | Phosphinite-oxazoline und metallkomplexe |
| DE10160142A1 (de) * | 2001-12-07 | 2003-06-18 | Basf Ag | Verfahren zur Herstellung von Tetrahydrogeraniol |
| DE102004049631A1 (de) * | 2004-10-11 | 2006-04-20 | Basf Ag | Verfahren zur Herstellung optisch aktiver Carbonylverbindungen |
-
2005
- 2005-12-20 ES ES05820633T patent/ES2371653T3/es not_active Expired - Lifetime
- 2005-12-20 US US11/793,729 patent/US8426617B2/en not_active Expired - Fee Related
- 2005-12-20 JP JP2007547315A patent/JP5090926B2/ja not_active Expired - Fee Related
- 2005-12-20 EP EP20050820633 patent/EP1828159B1/de not_active Expired - Lifetime
- 2005-12-20 AT AT05820633T patent/ATE520678T1/de not_active IP Right Cessation
- 2005-12-20 CN CN2005800445184A patent/CN101087774B/zh not_active Expired - Fee Related
- 2005-12-20 WO PCT/EP2005/013694 patent/WO2006066863A1/en not_active Ceased
-
2007
- 2007-07-20 KR KR1020077016839A patent/KR101342722B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008524288A (ja) | 2008-07-10 |
| KR20070089874A (ko) | 2007-09-03 |
| ES2371653T3 (es) | 2012-01-05 |
| JP5090926B2 (ja) | 2012-12-05 |
| WO2006066863A1 (en) | 2006-06-29 |
| CN101087774B (zh) | 2012-02-08 |
| EP1828159A1 (de) | 2007-09-05 |
| KR101342722B1 (ko) | 2013-12-19 |
| US20080039638A1 (en) | 2008-02-14 |
| EP1828159B1 (de) | 2011-08-17 |
| US8426617B2 (en) | 2013-04-23 |
| CN101087774A (zh) | 2007-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |