(S)-Proline esters and amides containing condensed aromatic rings were synthesised in order to use them as chiral modifiers in the enantioselective heterogeneous catalytic hydrogenation of isophorone and ethyl pyruvate. The (S)-proline 2-(2-naphthyl)-ethyl ester resulted in 23% enantiomeric excess of (S)-dihydroisophorone in methanol. 5% optical purity was obtained with the (S)-proline 3-ethyl-indolamide in the hydrogenation of ethyl pyruvate in acetic acid. (C) 2002 Elsevier Science B.V. All rights reserved.