A procedure for the synthesis of chirally-substituted cyclopentadienes has been developed by employing the intramol. Pauson-Khand reaction of chiral amides derived from 8-nonen-2-ynoic acid. Substrates included 1-[(2S)-2-(methoxymethyl)-1-pyrrolidinyl]-8-nonen-2-yn-1-one and N-[(1S)-1-phenylethyl]-8-nonen-2-ynamide. Hydride-mediated redn. of the resulting cyclopentenone adducts followed by acid-catalyzed dehydration leads to the formation of the corresponding cyclopentadienes in good overall yield. For example, the intramol. Pauson-Khand reaction of 1-[(2S)-2-(methoxymethyl)-1-pyrrolidinyl]-8-nonen-2-yn-1-one gave 3,3a,4,5,6,7-hexahydro-1-[[(2S)-2-(methoxymethyl)-1-pyrrolidinyl]carbonyl]-2H-inden-2-one (mixt. of diastereomers). The latter was elaborated into (4,5,6,7-tetrahydro-2H-inden-1-yl)[(2S)-2-(methoxymethyl)-1-pyrrolidinyl]methanone [i.e., a 4,5,6,7-tetrahydro-2H-indene-1-carboxamide deriv.]. [on SciFinder(R)]