FIELD: chemistry.
SUBSTANCE: invention relates to a method of obtaining optically active alcohols [(3R)-endo]- and [(3S)-exo]-1R,4S-2,2-dimethylcyclo[2.2.1]heptan-3-yl-methanols with general formula (1): [(3R)-endo] (1a) [(3S)-exo] (1b), which are used for obtaining enantiomerically pure products with high optical output. The method involves reacting camphene with a hydride bimetallic complex in form of a Zr,Al-hydride complex µ,µ-dihydro-bis[hydro-µ, chloro-diethylaluminium(bis-cyclopenta-dienylzirconium (IV))], at molar ratio camphene: [Cp2ZrH2*ClAlEt2]2:=2:1, in a benzole medium at 20°C, in an argon atmosphere for 2 hours, subsequent transmetalation of the organozirconium compound with ClAlEt2, oxidation of the reaction mass with dry oxygen and HCl decomposition.
EFFECT: method allows for stereoselective obtaining desired products under mild conditions.
1 ex
Title | Year | Author | Number |
---|---|---|---|
2-OXA-5-AZABICYCLO[2.2.1]HEPTANE-3-YL DERIVATIVES | 2015 |
|
RU2697651C2 |
BORONIC ACID DERIVATIVES | 2018 |
|
RU2793315C2 |
N-DIHYDROALKYLSUBSTITUTED 2-OXOIMIDAZOLE DERIVATIVES | 2006 |
|
RU2414456C2 |
SUBSTITUTED DIAMINOCARBOXAMIDE AND DIAMINOCARBONITRILE DERIVATIVES OF PYRIMIDINES, COMPOSITIONS THEREOF AND METHODS OF TREATING USE THEREOF | 2012 |
|
RU2697712C2 |
STEREOISOMERICALLY ENRICHED 3-AMINOCARBONYL BICYCLOHEPETENE PYRIMIDINE DIAMINES AND USE THEREOF | 2005 |
|
RU2416604C2 |
BENZOXAZOLONE DERIVATIVES SHOWING ANTIINFLAMMATORY ACTIVITY | 1991 |
|
RU2024512C1 |
LIGAND CONJUGATE WITH CYTOTOXIC DRUG PREPARATION, METHOD AND APPLICATION THEREOF | 2016 |
|
RU2708461C2 |
DIPEPTIDYL PEPTIDASE-4 INHIBITOR FOR TREATING TYPE 2 DIABETES MELLITUS, COMPOUNDS (VERSIONS) | 2018 |
|
RU2712097C1 |
SUBSTITUTED DIAMINO-CARBOXAMIDE AND DIAMINO-CARBONITRILE PYRIMIDINE DERIVATIVES, THEIR COMPOSITIONS AND METHODS OF TREATMENT USING THEM | 2012 |
|
RU2625309C2 |
METHOD OF SYNTHESIS OF BENZOXAZOLONE DERIVATIVES | 1990 |
|
RU2036913C1 |
Authors
Dates
2009-09-27—Published
2007-08-22—Filed