The regioselectivity of Pd-catalyzed malonate additions and arylations to cycloalkenyl esters canbe predicted by completing a stereochemical analysis of the Pd−π-allyl complex. The Pd-catalyzedmalonate additions which have the greatest degree of regioselectivity are in which substituentshave a steric influence in blocking the incoming nucleophile. Cyclopentenyl substrates displayedlower regioselectivity than the cyclohexyl counterparts presumably due to increased planarity ofthe system. Arylations using tin and hypervalent silicon reagents were compared.