CA2087035A1 - Ligands chiraux heterocycliques et methode de dihydroxylation asymetrique catalytique des olefines - Google Patents
Ligands chiraux heterocycliques et methode de dihydroxylation asymetrique catalytique des olefinesInfo
- Publication number
- CA2087035A1 CA2087035A1 CA002087035A CA2087035A CA2087035A1 CA 2087035 A1 CA2087035 A1 CA 2087035A1 CA 002087035 A CA002087035 A CA 002087035A CA 2087035 A CA2087035 A CA 2087035A CA 2087035 A1 CA2087035 A1 CA 2087035A1
- Authority
- CA
- Canada
- Prior art keywords
- olefin
- osmium
- combined
- derivative
- chiral ligand
- 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.)
- Granted
Links
- 150000001336 alkenes Chemical class 0.000 title abstract 7
- 239000003446 ligand Substances 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 5
- 238000006256 asymmetric dihydroxylation reaction Methods 0.000 title abstract 3
- 230000003197 catalytic effect Effects 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 6
- 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
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000012285 osmium tetroxide Substances 0.000 abstract 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 abstract 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
- C07C29/48—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
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69918391A | 1991-05-13 | 1991-05-13 | |
| US699,183 | 1991-05-13 | ||
| PCT/US1992/003940 WO1992020677A1 (fr) | 1991-05-13 | 1992-05-08 | Ligands chiraux heterocycliques et procede de dihydroxylation asymetrique et catalytique d'olefines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2087035A1 true CA2087035A1 (fr) | 1992-11-14 |
| CA2087035C CA2087035C (fr) | 2004-10-05 |
Family
ID=24808286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002087035A Expired - Lifetime CA2087035C (fr) | 1991-05-13 | 1992-05-08 | Ligands chiraux heterocycliques et methode de dihydroxylation asymetrique catalytique des olefines |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0543969A1 (fr) |
| JP (2) | JP3550397B2 (fr) |
| CA (1) | CA2087035C (fr) |
| WO (1) | WO1992020677A1 (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5491237A (en) * | 1994-05-03 | 1996-02-13 | Glaxo Wellcome Inc. | Intermediates in pharmaceutical camptothecin preparation |
| US6313247B1 (en) | 1996-06-05 | 2001-11-06 | Wolfgang Lindner | Cinchonan based chiral selectors for separation of stereoisomers |
| US6559309B2 (en) | 1996-11-01 | 2003-05-06 | Osi Pharmaceuticals, Inc. | Preparation of a camptothecin derivative by intramolecular cyclisation |
| WO1998035927A1 (fr) * | 1997-02-14 | 1998-08-20 | The Scripps Research Institute | Ligands alcaloides lies a du polyethyleneglycol et utilisation de ces derniers |
| US6646102B2 (en) | 2001-07-05 | 2003-11-11 | Dow Global Technologies Inc. | Process for manufacturing an alpha-dihydroxy derivative and epoxy resins prepared therefrom |
| US8987504B2 (en) | 2010-06-18 | 2015-03-24 | Victoria Link Limited | Aminohydroxylation of alkenes |
| US20120220729A1 (en) | 2011-02-28 | 2012-08-30 | Boehringer Ingelheim International Gmbh | Liquid phase separation of plasmid dna isoforms and topoisomers |
| JPWO2014148591A1 (ja) * | 2013-03-21 | 2017-02-16 | 国立大学法人名古屋大学 | １，２−ジオール化合物の製造方法 |
| CN110642856B (zh) * | 2019-10-21 | 2020-10-02 | 河南科技大学 | 二氢奎尼丁类化合物及其制备方法和应用、植物源杀虫剂 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5126494A (en) * | 1988-01-11 | 1992-06-30 | Massachusetts Institute Of Technology | Methods for catalytic asymmetric dihydroxylation of olefins |
| ATE128449T1 (de) * | 1988-01-11 | 1995-10-15 | Massachusetts Inst Technology | Durch komplexmittel beschleunigte katalytische asymmetrische dihydroxylierung. |
-
1992
- 1992-05-08 CA CA002087035A patent/CA2087035C/fr not_active Expired - Lifetime
- 1992-05-08 JP JP50013693A patent/JP3550397B2/ja not_active Expired - Fee Related
- 1992-05-08 EP EP92912059A patent/EP0543969A1/fr not_active Ceased
- 1992-05-08 WO PCT/US1992/003940 patent/WO1992020677A1/fr not_active Ceased
-
2004
- 2004-01-07 JP JP2004002364A patent/JP3924282B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004168783A (ja) | 2004-06-17 |
| JPH06500344A (ja) | 1994-01-13 |
| EP0543969A1 (fr) | 1993-06-02 |
| WO1992020677A1 (fr) | 1992-11-26 |
| JP3550397B2 (ja) | 2004-08-04 |
| JP3924282B2 (ja) | 2007-06-06 |
| CA2087035C (fr) | 2004-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2081315A1 (fr) | Ligands chiraux heterocycliques et methode de dihydroxylation catalytique asymetrique d'olefines | |
| DE69233299D1 (de) | Liganden für asymmetrische dihydroxylierung: mehrere cinchona alkaloid einheiten gebunden an einen zentralen heterozyklischen kern | |
| Xu et al. | Bifunctional‐Thiourea‐Catalyzed Diastereo‐and Enantioselective Aza‐Henry Reaction | |
| Morimoto et al. | An improved diphosphine-iridium (I) catalyst system for the asymmetric hydrogenation of cyclic imines: Phthalimide as an efficient co-catalyst | |
| CA2087035A1 (fr) | Ligands chiraux heterocycliques et methode de dihydroxylation asymetrique catalytique des olefines | |
| Yoshioka et al. | Asymmetric induction catalyzed by conjugate bases of chiral proton acids as ligands: Enantioselective addition of dialkylzinc-orthotitanate complex to benzaldehyde with catalytic ability of a remarkable high order | |
| DE68924418D1 (de) | Durch komplexmittel beschleunigte katalytische asymmetrische dihydroxylierung. | |
| Yasui et al. | Model studies with nicotinamide derivatives | |
| CA2077541A1 (fr) | Catalyseurs chiraux et reactions d'epoxydation catalysees par ces derniers | |
| CA2259203A1 (fr) | Methode de synthese d'amines et d'acides amines avec des derives organobores | |
| WO2001049790A3 (fr) | Colorants a base de cyanine a modification de mobilite | |
| CA2082166A1 (fr) | Catalyseurs de type metal de transition a base de derives chiraux de phospholanes | |
| Knox et al. | Tertiary amine lewis base catalysis in combination with transition metal catalysis | |
| CA2272716A1 (fr) | Dedoublement d'un sel d'acide ritalinique | |
| DE69936095D1 (de) | Verfahren zur herstellung eines porphyrin-metallkomplexes | |
| WO2004069394A3 (fr) | Procede synthetique d'arylation directe d'arenes heterocycliques | |
| RU93058546A (ru) | Способ получения производных эрголина, фармацевтическая композиция | |
| Grotjahn et al. | Coordination of chiral amines to coordinatively unsaturated Cp∗ Ir-amino acid complexes allows determination of enantiomeric purity | |
| IT8519168A0 (it) | Procedimento di elettrocarbossilazione di composti carbonilici per la produzione di acidi, idrossi-carbossilici. | |
| DK161759C (da) | Hydrostatisk styreindretning, isaer til motordrevne koeretoejer | |
| DE58903584D1 (de) | Vorrichtung zum sperren der lenkung eines kraftfahrzeugs. | |
| WO2000021663A3 (fr) | Ligands phosphoreux sur supports polymeres destines a la catalyse | |
| US7642357B2 (en) | Iridium complexes | |
| JP2008526940A5 (fr) | ||
| Hamashima et al. | Scope and Mechanism of Tandem Aza‐Michael Reaction/Enantioselective Protonation Using a Pd–μ‐Hydroxo Complex under Mild Conditions Buffered with Amine Salts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKEC | Expiry (correction) |
Effective date: 20121202 |