Enantioselective syntheses of 2-arylpropanoic acid non-steroidal antiinflammatory drugs and related compounds.
1995; Elsevier BV; Volume: 51; Issue: 46 Linguagem: Inglês
10.1016/0040-4020(95)00805-i
ISSN1464-5416
AutoresD. P. G. HAMON, R. A. MASSY‐WESTROPP, Josephine L. Newton,
Tópico(s)Chemical Synthesis and Reactions
Resumo(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-iodophenyl)propanoic and 2-(4-iodophenyl)propanoic acids, prepared by the methodology above, is a general method for the synthesis of optically active arylpropanoic acids.
Referência(s)