ENANTIOSELECTIVE SYNTHESES OF 2-ARYLPROPANOIC ACID NONSTEROIDAL ANTIINFLAMMATORY DRUGS AND RELATED-COMPOUNDS

(S)-2-[4'-(2''-Methylpropyl)phenylpropanoic acid (ibuprofen) and (S)-2 -(3'-benzoylphenyl)propanoic acid (ketoprofen) have been synthesised i n high enantiomeric excess. Control of stereochemistry was achieved by a combination of Sharpless epoxidation followed by catalytic hydrogen olysis of the introduced benzylic epoxide oxygen bond. Also, the coupl ing of organic compounds in the presence of palladium with enantiopure 2-(3-iodophenyl)propanoic and 2-(4-iodophenyl)propanoic acids, prepar ed by the methodology above, is a general method for the synthesis of optically active arylpropanoic acids.