An iridium-catalyzed enantioselective hydroalkynylation of alpha,beta-unsaturated amides was described. The selectivity of this reaction is distinct from that observed in many catalytic hydroalkynylations of alpha,beta-unsaturated carbonyl compounds. It occurs selectively at the gamma instead of the beta position. Preliminary mechanistic studies suggest that the reaction proceeds through alkene isomerization followed by hydroalkynylation. This method provides a straightforward route for the synthesis of amides with a remote stereocenter at the gamma position.