An Ir-catalyzed tandem olefination/aza-Michael reaction of protected benzoylhydrazine derivatives with olefins under mild conditions has been developed. This method can be successfully applied to the construction of various structurally N-N-functionalized hydrazide derivatives bearing the α,β-unsaturated side chain in good to excellent yields. In particular, the deaminoprotected products can be used as potential precursors for the construction of N-N axially chiral compounds.