Recently, our group demonstrated that the readily available and bench-stable imidazolidines could serve as potent 1,5-dipole equivalents, with one of the N-atom acting as nucleophile and the aminal carbon as electrophile. In the course of our studies, we envision that a transition-metal-catalyzed (5+1) cycloaddition of diazooxindoles with imidazolidines should be feasible via a metallocarbene formation (I)/nucleophilic addition (II)/aminal ringopening (III)/intramolecular cyclization sequence to form the target spirooxindole-piperazine scaffolds (Scheme 1C). However, to further realize the asymmetric version, Hu's cooperative catalysis strategy is not suitable for this reaction because CPA can not activate the iminium group of intermediate III. Thus, one can imagine that an organometallic catalysis seems possible (Scheme 1C, path a), while a big challenge is to avoid the freeylide pathway (Scheme 1C, path b), in which a metal-free ammonium ylide intermediate II' is formed that would result in no chiral induction at the last ring-closure process (stereocenterformation step). To meet this challenge, herein, we reported a (5+1) cycloaddition of diazooxindoles with imidazolidines to access a library of spirooxindole-piperazines in moderate to excellent yields under rhodium or copper catalysis. Moreover, the asymmetric version was also realized by employing the combination of Cu(OTf)2 and a newly synthesized SaBOX ligand L5, leading to optically active products with up to 93:7 e.r. (Scheme 1D).