Tetrahedron

Enantioselective syntheses of 2-arylpropanoic acid non-steroidal antiinflammatory drugs and related compounds.

DPG Hamon, RA Massy-Westropp, JL Newton

Index: Hamon, David P.G.; Massy-Westropp, Ralph A.; Newton, Josephine L. Tetrahedron, 1995 , vol. 51, # 46 p. 12645 - 12660

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Citation Number: 19

Abstract

(S)-2-[4′-(2 ″-Methylpropyl) phenylpropanoic acid (ibuprofen) and (S)-2-(3′- benzoylphenyl) propanoic acid (ketoprofen) have been synthesised in high enantiomeric excess. Control of stereochemistry was achieved by a combination of Sharpless epoxidalion followed by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond. Also, the coupling of organic compounds in the presence of palladium with enantiopure 2-(3- ...