EA033435B1 - Применение смесей e/z-изомеров для количественного получения определенных продуктов сочетанием асимметрической гидрогенизации и изомеризации - Google Patents
Применение смесей e/z-изомеров для количественного получения определенных продуктов сочетанием асимметрической гидрогенизации и изомеризацииInfo
- Publication number
- EA033435B1 EA033435B1 EA201500662A EA201500662A EA033435B1 EA 033435 B1 EA033435 B1 EA 033435B1 EA 201500662 A EA201500662 A EA 201500662A EA 201500662 A EA201500662 A EA 201500662A EA 033435 B1 EA033435 B1 EA 033435B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- iii
- isomers
- isomerization
- mixtures
- asymmetric hydrogenation
- Prior art date
Links
Classifications
-
- 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
- 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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/60—Preparation of compounds having groups or groups
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
Abstract
Изобретение касается способа получения соединений, содержащих стереогенные центры, из смеси E/Z-изомеров ненасыщенных соединений, содержащих прохиральные двойные связи, путем гидрогенизации соответствующего изомера молекулярным водородом в присутствии хирального комплекса иридия формулы (III), выбираемой из формул (III-C), (III-D) и (III-F), где группы и символы в указанных формулах имеют значения, которые определены в настоящем описании. Продукты гидрогенизации обладают заданной конфигурацией по стереогенным центрам. Способ включает стадию асимметрической гидрогенизации и стадию изомеризации. Способ дает большие преимущества тем, что в нем из смеси стереоизомеров исходного соединения эффективно образуется требуемый хиральный продукт.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12197857 | 2012-12-18 | ||
PCT/EP2013/077246 WO2014096107A1 (en) | 2012-12-18 | 2013-12-18 | Using mixtures of e/z isomers to obtain quantitatively specific products by combining asymmetric hydrogenation and isomerization |
Publications (2)
Publication Number | Publication Date |
---|---|
EA201500662A1 EA201500662A1 (ru) | 2015-12-30 |
EA033435B1 true EA033435B1 (ru) | 2019-10-31 |
Family
ID=47500977
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EA201500662A EA033435B1 (ru) | 2012-12-18 | 2013-12-18 | Применение смесей e/z-изомеров для количественного получения определенных продуктов сочетанием асимметрической гидрогенизации и изомеризации |
Country Status (8)
Country | Link |
---|---|
US (1) | US9573872B2 (ru) |
EP (1) | EP2935189B1 (ru) |
JP (1) | JP6406676B2 (ru) |
CN (1) | CN104884420A (ru) |
BR (1) | BR112015014204B1 (ru) |
EA (1) | EA033435B1 (ru) |
ES (1) | ES2739229T3 (ru) |
WO (1) | WO2014096107A1 (ru) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9561989B2 (en) * | 2012-12-18 | 2017-02-07 | Dsm Ip Assets B.V. | Process of asymmetric hydrogenation of ketals and acetals |
EP2935185B1 (en) * | 2012-12-18 | 2019-02-20 | DSM IP Assets B.V. | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one |
BR112015014335B1 (pt) * | 2012-12-18 | 2020-12-08 | Dsm Ip Assets B.V. | (6r,10r)-6,10,14-trimetilpentadecan-2-ona preparada a partir de 6,10-dimetilundec-5-en-2-ona ou 6,10 dimetilundeca-5,9-dien-2-ona |
US9458076B2 (en) * | 2012-12-18 | 2016-10-04 | Dsm Ip Assets B.V. | Using mixtures of E/Z isomers to obtain quantitatively specific products by combined asymmetric hydrogenations |
US20210009495A1 (en) * | 2018-02-13 | 2021-01-14 | Basf Se | Method for the isomerization of a 3-(z)-unsaturated carboxylic acid to the 3-(e)-isomer |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2302996A1 (fr) * | 1974-09-02 | 1976-10-01 | Kuraray Co | Procede pour preparer des isomeres stereospecifiques de l'acide farnesylacetique, de ses esters et de leurs derives |
EP1179531A1 (en) * | 2000-08-11 | 2002-02-13 | Aventis Animal Nutrition S.A. | Intermediates for use in the preparation of vitamin E |
WO2006066863A1 (en) * | 2004-12-22 | 2006-06-29 | Dsm Ip Assets B.V. | Asymmetric hydrogenation of alkennes using chiral iridium complexes |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL295084A (ru) | 1962-07-11 | 1900-01-01 | ||
DE2455975A1 (de) * | 1973-11-30 | 1975-07-10 | Firmenich & Cie | Verwendung von neuen acetalen als riech- und geschmacksstoffe |
GB1479272A (en) | 1974-12-23 | 1977-07-13 | Kuraray Co | Process for preparing a stereospecific farnesol |
JPS6036479A (ja) * | 1983-08-08 | 1985-02-25 | Kotobuki Seiyaku Kk | 1,3−ジオキサン誘導体、本化合物を有効成分とする抗潰瘍剤及びその製造方法 |
JP2771866B2 (ja) * | 1989-11-01 | 1998-07-02 | エーザイ株式会社 | 不飽和テルペン類の製造方法 |
JP3725233B2 (ja) * | 1995-04-18 | 2005-12-07 | 株式会社カネボウ化粧品 | トレハロース誘導体及び界面活性剤 |
US5908957A (en) * | 1997-02-14 | 1999-06-01 | Roche Vitamins Inc. | Isomerization process |
EP2269998A3 (en) | 2004-08-19 | 2011-03-30 | DSM IP Assets B.V. | Process for the rectification of mixtures of high-boiling air- and/or temperature-sensitive useful products |
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 |
WO2010006954A1 (en) * | 2008-07-15 | 2010-01-21 | Dsm Ip Assets B.V. | Novel n-substituted beta-amino acid esters |
EP2543437A4 (en) * | 2010-03-04 | 2014-09-03 | Takasago Perfumery Co Ltd | HOMOGENEOUS ASYMMETRIC HYDROGENATION CATALYST |
US9458076B2 (en) * | 2012-12-18 | 2016-10-04 | Dsm Ip Assets B.V. | Using mixtures of E/Z isomers to obtain quantitatively specific products by combined asymmetric hydrogenations |
EP2935185B1 (en) * | 2012-12-18 | 2019-02-20 | DSM IP Assets B.V. | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10,14-trimetylpentadeca-5,9,13-trien-2-one or 6,10,14-trimetylpentadeca-5,9-dien-2-one |
BR112015014335B1 (pt) * | 2012-12-18 | 2020-12-08 | Dsm Ip Assets B.V. | (6r,10r)-6,10,14-trimetilpentadecan-2-ona preparada a partir de 6,10-dimetilundec-5-en-2-ona ou 6,10 dimetilundeca-5,9-dien-2-ona |
-
2013
- 2013-12-18 US US14/652,362 patent/US9573872B2/en active Active
- 2013-12-18 EP EP13814522.2A patent/EP2935189B1/en active Active
- 2013-12-18 JP JP2015547087A patent/JP6406676B2/ja active Active
- 2013-12-18 EA EA201500662A patent/EA033435B1/ru not_active IP Right Cessation
- 2013-12-18 ES ES13814522T patent/ES2739229T3/es active Active
- 2013-12-18 WO PCT/EP2013/077246 patent/WO2014096107A1/en active Application Filing
- 2013-12-18 BR BR112015014204-4A patent/BR112015014204B1/pt active IP Right Grant
- 2013-12-18 CN CN201380065928.1A patent/CN104884420A/zh active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2302996A1 (fr) * | 1974-09-02 | 1976-10-01 | Kuraray Co | Procede pour preparer des isomeres stereospecifiques de l'acide farnesylacetique, de ses esters et de leurs derives |
EP1179531A1 (en) * | 2000-08-11 | 2002-02-13 | Aventis Animal Nutrition S.A. | Intermediates for use in the preparation of vitamin E |
WO2006066863A1 (en) * | 2004-12-22 | 2006-06-29 | Dsm Ip Assets B.V. | Asymmetric hydrogenation of alkennes using chiral iridium complexes |
Non-Patent Citations (5)
Title |
---|
ARAVAMUDAN S. GOPALAN, ROBERT PRIETO, BRITTA MUELLER, DAVID PETERS: "Polyene cyclizations using mercury (II) triflate-N,N-dimethylaniline complex - participation by internal nucleophiles", TETRAHEDRON LETTERS, PERGAMON, vol. 33, no. 13, 1 March 1992 (1992-03-01), pages 1679 - 1682, XP055058597, ISSN: 00404039, DOI: 10.1016/S0040-4039(00)91704-0 * |
CHEMICAL ABSTRACTS, 7 January 1997, Columbus, Ohio, US; IKEMOTO TAKESHI, ET AL: "Preparation of 4,6-O-alkylidene-.alpha.,.alpha.-trehalose as surfactants" XP002697173 * |
JUSTICIA, J. OLTRA, J.E. CUERVA, J.M.: "Palladium mediated C-H activation in the field of terpenoids: synthesis of rostratone", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 45, no. 22, 24 May 2004 (2004-05-24), AMSTERDAM, NL, pages 4293 - 4296, XP004506345, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2004.04.005 * |
TOSHIO KUBOTA, SATOSHI MIYASHITA, TOMOYA KITAZUME, NOBUO ISHIKAWA: "Novel synthetic reactions using bis(2,2,2-trifluoroethoxy)triphenylphosphorane", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY �ETC.|, vol. 45, no. 25, 1 December 1980 (1980-12-01), pages 5052 - 5057, XP055105066, ISSN: 00223263, DOI: 10.1021/jo01313a008 * |
YOSHIHARU MATSUBARA; TANIICHIRO YAMAGA; KOJI TSUJIKAWA; SHOJI WAKABAYASHI: "Synthesis of New Acetals and their Derivatives from Terpene Aldehyde and Alcohol", YUKI GOSEI KAGAKU KYOKAISHI - JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY. JAPAN., YUKI GOSEI KAGAKU KAOKAI, TOKYO., JP, vol. 28, no. 8, 1 January 1970 (1970-01-01), JP, pages 849 - 852, XP002694891, ISSN: 0037-9980, DOI: 10.5059/yukigoseikyokaishi.28.849 * |
Also Published As
Publication number | Publication date |
---|---|
US20160185702A1 (en) | 2016-06-30 |
JP2016505568A (ja) | 2016-02-25 |
BR112015014204B1 (pt) | 2021-03-30 |
JP6406676B2 (ja) | 2018-10-17 |
EP2935189A1 (en) | 2015-10-28 |
EP2935189B1 (en) | 2019-06-12 |
US9573872B2 (en) | 2017-02-21 |
WO2014096107A1 (en) | 2014-06-26 |
EA201500662A1 (ru) | 2015-12-30 |
ES2739229T3 (es) | 2020-01-29 |
BR112015014204A2 (pt) | 2017-07-11 |
CN104884420A (zh) | 2015-09-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JOP20210064A1 (ar) | عملية لتحضير 5- فلورو-1h- بيرازولوبيريدينات مستبدلة | |
EA033435B1 (ru) | Применение смесей e/z-изомеров для количественного получения определенных продуктов сочетанием асимметрической гидрогенизации и изомеризации | |
PH12015500644A1 (en) | Novel rig-i ligands and methods for producing them | |
MX2014004055A (es) | Proceso para la preparacion de metoximelonal. | |
IN2014DN08668A (ru) | ||
MX2017001459A (es) | Sintesis de fosforamidatos. | |
EA201500646A1 (ru) | Применение смесей e/z-изомеров для количественного получения определенных продуктов посредством комбинированной асимметрической гидрогенизации | |
MY195300A (en) | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 6,10-dimetylundec-5-en-2-one or 6,10-dimetylundeca-5,9-dien-2-one | |
MX2017005630A (es) | Metodo para preparar bifenilaminas a partir de azobencenos mediante catalisis de rutenio. | |
EA033302B9 (ru) | (6r,10r)-6,10,14-триметилпентадекан-2-он, получаемый из 6,10,14-триметилпентадека-5,9,13-триен-2-она или 6,10,14-триметилпентадека-5,9-диен-2-она | |
MX2015012249A (es) | Metodo para producir cis-1-cloro-3,3,3-trifluoropropeno. | |
MY171808A (en) | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from 3,7-dimetyloct-2-enal or 3,7-dimetylocta-2,6-dienal | |
MX2020001431A (es) | Proceso para preparar un enol eter biciclico. | |
MX2013004872A (es) | Procesos para preparar un fenilciclohexano. | |
IN2014DN08226A (ru) | ||
WO2013080049A3 (en) | A process for the manufacture of chiral catalysts and their salts | |
MY195029A (en) | (6R,10R)-6,10,14-Trimetylpentadecan-2-One Prepared From 6,10-Dimetylundeca-3,5,9-Trien-2-One | |
BR112014018492A8 (pt) | Processo aperfeiçoado para a produção de etileno 1,1-disubstituído | |
BR112016022312A2 (pt) | Método para a produção de um produto químico | |
IN2014DN09213A (ru) | ||
MY174887A (en) | (6r,10r)-6,10,14-trimetylpentadecan-2-one prepared from (r)-3,7-dimetyloct-6-enal | |
MY195032A (en) | (6R,10R)-6,10,14-Trimetylpentadecan-2-One Prepared From (R)-6,10,14-Trimetylpentadec-5-en-2-One | |
TH151545A (th) | กระบวนการสำหรับการผลิตของ 1,3-บิวทาไดอีน | |
MY180398A (en) | A process for the production of oligomerized olefins |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG TJ TM RU |