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), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:11; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ALCOHOLS
CARBOXYLIC ACID ESTERS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHROMATOGRAPHY
ENANTIOMORPHS
EPOXIDES
ESTERS
HYDROXY COMPOUNDS
INORGANIC ION EXCHANGERS
ION EXCHANGE MATERIALS
KINETICS
MATERIALS
MINERALS
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
REACTION KINETICS
SEPARATION PROCESSES
SPECTRA
SYNTHESIS
THIN-LAYER CHROMATOGRAPHY
TITANIUM COMPOUNDS
TRANSITION ELEMENT COMPOUNDS
YIELDS
ZEOLITES