ATE178578T1 - Durch einen komplexbilder beschleunigte asymmetrische katalytische dihydroxylierung - Google Patents
Durch einen komplexbilder beschleunigte asymmetrische katalytische dihydroxylierungInfo
- Publication number
- ATE178578T1 ATE178578T1 AT95200458T AT95200458T ATE178578T1 AT E178578 T1 ATE178578 T1 AT E178578T1 AT 95200458 T AT95200458 T AT 95200458T AT 95200458 T AT95200458 T AT 95200458T AT E178578 T1 ATE178578 T1 AT E178578T1
- Authority
- AT
- Austria
- Prior art keywords
- olefin
- osmium
- combined
- derivative
- asymmetric
- Prior art date
Links
- 230000003197 catalytic effect Effects 0.000 title 1
- 238000005906 dihydroxylation reaction Methods 0.000 title 1
- 150000001336 alkenes Chemical class 0.000 abstract 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 6
- 239000003446 ligand Substances 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- 229910052762 osmium Inorganic materials 0.000 abstract 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- LJOQGZACKSYWCH-LHHVKLHASA-N (s)-[(2r,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol Chemical class C1=C(OC)C=C2C([C@H](O)[C@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 LJOQGZACKSYWCH-LHHVKLHASA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 238000006256 asymmetric dihydroxylation reaction Methods 0.000 abstract 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 abstract 2
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 abstract 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract 1
- 239000012285 osmium tetroxide Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
-
- 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
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/26—Polyhydroxylic alcohols containing only six-membered aromatic rings as cyclic part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
-
- 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
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
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)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14269288A | 1988-01-11 | 1988-01-11 | |
| US07/159,068 US4871855A (en) | 1988-01-11 | 1988-02-23 | Ligand-accelerated catalytic asymmetric dihydroxylation using dihydroquinidine and dihydroquinidine esters as ligands |
| US07/250,378 US4965364A (en) | 1988-02-23 | 1988-09-28 | Ligand-accelerated catalytic asymmetric dihydroxylation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE178578T1 true ATE178578T1 (de) | 1999-04-15 |
Family
ID=27385846
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT89901900T ATE128449T1 (de) | 1988-01-11 | 1989-01-10 | Durch komplexmittel beschleunigte katalytische asymmetrische dihydroxylierung. |
| AT95200458T ATE178578T1 (de) | 1988-01-11 | 1989-01-10 | Durch einen komplexbilder beschleunigte asymmetrische katalytische dihydroxylierung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT89901900T ATE128449T1 (de) | 1988-01-11 | 1989-01-10 | Durch komplexmittel beschleunigte katalytische asymmetrische dihydroxylierung. |
Country Status (6)
| Country | Link |
|---|---|
| EP (2) | EP0395729B1 (de) |
| JP (2) | JP3153540B2 (de) |
| AT (2) | ATE128449T1 (de) |
| CA (1) | CA1338314C (de) |
| DE (2) | DE68928969T2 (de) |
| WO (1) | WO1989006225A1 (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5227543A (en) * | 1988-01-11 | 1993-07-13 | Massachusetts Institute Of Technology | Facilitation of turnover in the ADH by additives which catalyze the hydrolysis of the OS(VI) glycolate esters |
| US5260461A (en) * | 1988-01-11 | 1993-11-09 | Massachusetts Institute Of Technology | Ligands for ADH: cinchona alkaloids and moderately sized organic substituents linked through a planar aromatic spacer group |
| US5126494A (en) * | 1988-01-11 | 1992-06-30 | Massachusetts Institute Of Technology | Methods for catalytic asymmetric dihydroxylation of olefins |
| US5516929A (en) * | 1988-01-11 | 1996-05-14 | Massachusetts Institute Of Technology | Method for catalytic asymmetric dihydroxylation of olefins using heterocyclic chiral ligands |
| CA2087035C (en) * | 1991-05-13 | 2004-10-05 | K. Barry Sharpless | Heterocyclic chiral ligands and method for catalytic asymmetric dihydroxylation of olefins |
| US5491237A (en) | 1994-05-03 | 1996-02-13 | Glaxo Wellcome Inc. | Intermediates in pharmaceutical camptothecin preparation |
| US6559309B2 (en) | 1996-11-01 | 2003-05-06 | Osi Pharmaceuticals, Inc. | Preparation of a camptothecin derivative by intramolecular cyclisation |
| AU5710198A (en) * | 1996-12-18 | 1998-07-15 | Scripps Research Institute, The | Catalytic asymmetric amidohydroxylation of olefins with n-halo carboxamides |
| WO2000063173A1 (en) * | 1999-04-14 | 2000-10-26 | F. Hoffmann-La Roche Ag | Process for the preparation of substituted piperidines |
| DE19920039A1 (de) | 1999-04-25 | 2000-10-26 | Bayer Ag | Verfahren zur asymmetrischen Dihydroxylierung von Olefinen mittels Osmium-Katalysatoren |
| US8987504B2 (en) | 2010-06-18 | 2015-03-24 | Victoria Link Limited | Aminohydroxylation of alkenes |
| WO2012092512A2 (en) * | 2010-12-31 | 2012-07-05 | California Institute Of Technology | Catalytic anti-markovnikov oxidation and hydration of olefins |
| CN102531911B (zh) * | 2011-12-22 | 2016-02-17 | 浙江工业大学 | 手性二环类化合物及其不对称合成方法 |
| US10723672B2 (en) | 2018-02-26 | 2020-07-28 | Chervon Phillips Chemical Company Lp | Normal alpha olefin synthesis using dehydroformylation or dehydroxymethylation |
| US11123723B2 (en) | 2018-02-26 | 2021-09-21 | The Regents Of The University Of California | Oxidative dehydroxymethylation of alcohols to produce olefins |
| EP3546447A1 (de) * | 2018-03-29 | 2019-10-02 | Heidelberg Pharma GmbH | Synthese von (2s,3r,4r)-4,5-dihydroxyisoleucin und derivaten |
-
1989
- 1989-01-10 AT AT89901900T patent/ATE128449T1/de not_active IP Right Cessation
- 1989-01-10 WO PCT/US1989/000086 patent/WO1989006225A1/en not_active Ceased
- 1989-01-10 AT AT95200458T patent/ATE178578T1/de active
- 1989-01-10 EP EP89901900A patent/EP0395729B1/de not_active Expired - Lifetime
- 1989-01-10 JP JP50181489A patent/JP3153540B2/ja not_active Expired - Lifetime
- 1989-01-10 EP EP95200458A patent/EP0658532B1/de not_active Expired - Lifetime
- 1989-01-10 DE DE68928969T patent/DE68928969T2/de not_active Expired - Lifetime
- 1989-01-10 DE DE68924418T patent/DE68924418T2/de not_active Expired - Lifetime
- 1989-01-11 CA CA000587964A patent/CA1338314C/en not_active Expired - Fee Related
-
2000
- 2000-11-02 JP JP2000335775A patent/JP2001192383A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP0658532A1 (de) | 1995-06-21 |
| WO1989006225A1 (en) | 1989-07-13 |
| JPH03503885A (ja) | 1991-08-29 |
| EP0658532B1 (de) | 1999-04-07 |
| DE68924418D1 (de) | 1995-11-02 |
| EP0395729B1 (de) | 1995-09-27 |
| DE68928969T2 (de) | 1999-12-16 |
| DE68928969D1 (de) | 1999-05-12 |
| EP0395729A1 (de) | 1990-11-07 |
| JP2001192383A (ja) | 2001-07-17 |
| CA1338314C (en) | 1996-05-07 |
| JP3153540B2 (ja) | 2001-04-09 |
| ATE128449T1 (de) | 1995-10-15 |
| DE68924418T2 (de) | 1996-03-28 |
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