Catalytic asymmetric epoxidation of methyl 7-hydroxy-5E-heptenoate
The principal chiral synthon in the synthesis of optically active leucotriene A/sub 4/ is methyl 5S,6S-epoxy-7-hydroxyheptanoate (II), the simplest method for the production of which is asymmetric epoxidation of allyl alcohols by tert-butyl hydroperoxide in the presence of equimolar amounts of titanium tetraisopropoxide and optically active tertaric ester (1-3). However, in the case of methyl 7-hydroxy-5E-heptenoate (I) the good solubility of the epoxy alcohol (II) in water hinders its isolation from the reaction mixture. A method of catalytic asymmetric epoxidation has now been developed which makes it possible to simplify the isolation of the reaction product significantly. The authors have found that the catalytic oxidation can be used successfully for the synthesis of the above-mentioned alcohol (II) and makes it possible to obtain it with high enantiomeric purity. The reaction is monitored by TLC. They modified the procedure for the isolation of the epoxy alcohol (II).
- Research Organization:
- Institute of Organic Chemistry, Kiev (USSR)
- OSTI ID:
- 5949522
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 23:11; Other Information: Translated from Zh. Org. Khim.; 23: No. 11, 2470-2471 (Nov 1987)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ALCOHOLS
CATALYSIS
CARBOXYLIC ACID ESTERS
CATALYTIC EFFECTS
HYDROXY COMPOUNDS
TITANIUM COMPOUNDS
ZEOLITES
CATALYSTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
ENANTIOMORPHS
EPOXIDES
NMR SPECTRA
SYNTHESIS
THIN-LAYER CHROMATOGRAPHY
CHROMATOGRAPHY
ESTERS
INORGANIC ION EXCHANGERS
ION EXCHANGE MATERIALS
KINETICS
MATERIALS
MINERALS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
REACTION KINETICS
SEPARATION PROCESSES
SPECTRA
TRANSITION ELEMENT COMPOUNDS
YIELDS
400201* - Chemical & Physicochemical Properties