Propargylic esters derived from cyclic ketones containing a tethered aldehyde generate bicyclic homopropargyl alcohols upon treatment with Et2Zn in the presence of a catalytic amount of Pd(0). The reaction is thought to involve an intramolecular carbonyl addition of intermediate allenylzinc nucleophilic species generated from the propargylic ester functionality. The resulting trisubstituted bicyclic products are obtained with high stereoselectivity. Examples are provided where the reaction is successfully applied to both cyclopentanone-and cyclohexanone-derived substrates containing either terminal or internal alkyne, thus overcoming some of the limitations previously encountered with the use of alternative methodology.