In summary, we have developed a catalytic (5+1) cycloaddition of diazooxindoles with imidazolidines, establishing a general and efficient strategy to construct a library of spirooxindolepiperazines in moderate to excellent yields under rhodium or copper catalysis. Moreover, diverse transformations of the obtained products have been achieved to access more complex and even drug-derived spirooxindoles. Importantly, the asymmetric version has also been realized by employing Cu(OTf)2 and a newly synthesized SaBOX ligand L5. This report proves that rhodium and copper are complementary catalysts for this reaction, and that copper is more competent than rhodium in catalytic asymmetric reactions involving diazocarbene-ylide intermediates. We believe that this report would significantly enrich the toolbox of both medicinal chemists and synthetic chemists. Further studies will be reported in due course.