An efficient palladium-catalyzed [2 + 1]cycloaddition between ynamides and norbornenes or norbornadienes is reported. Both phosphapalla- dacycles and palladium/secondary phosphine oxide catalytic systems were found to be competent for the transformation allowing the preparation of ami- nomethylenecyclopropanes. The reaction showed general applicability to various functionalized bicyclo[2.2.1]hept-2-enes and ynamides. A chiral phosphapalladacycle was tested to carry out this transformation in an enantioselective fashion.