Palladium-catalysed enantioselective synthesis of ibuprofen

Reference:

Acemoglu, L. and Williams, J. M. J., 2003. Palladium-catalysed enantioselective synthesis of ibuprofen. Journal of Molecular Catalysis A: Chemical, 196 (1-2), pp. 3-11.

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Abstract

A general strategy has been developed for the enantioselective synthesis of alpha-aryl propanoic acids. Palladium-catalysed asymmetric allylic substitution is used as the key step of the synthesis. Compound 2a was obtained in 95% ee from the allylic substitution reaction of 1,3-diphenylprop-2-enyl acetate la with bis(phenylsulfonyl)methane, catalysed by palladium and oxazoline ligand 9. Ozonolysis, desulfonylation followed by oxidation furnished (S)-2-phenylpropanoic acid 4a without detectable loss of enantiomeric purity. The same synthetic strategy was employed to obtain Ibuprofen 4b in 87% ee, starting from acetate 1b. (C) 2002 Elsevier Science B.V. All rights reserved.

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