A Rh(II)-catalyzed chemoselective oxidative amination and cyclization cascade of 1-(arylethynyl)cycloalkyl)methyl sulfamates has been presented. For a cyclopropyl or cyclobutyl moiety containing alkynyl sulfamates, the reactions underwent a metallonitrene-initiated alkyne oxidation along with cyclopropyl ring expansion or alkoxyl moiety migration to give cyclobutane-fused or methylenecyclobutane-containing heterocycles. In the case of a cyclopentyl or cyclohexyl moiety containing sulfamate, the reaction underwent a direct C-H bond insertion event to afford the corresponding nitrogen-containing heterocyclic product.