Spirooxindoles represent as privileged synthetic targets because of their prevalence in numerous natural products and pharmacologically relevant drugs. Among them, the sixmembered N-heterocyclic spirooxindoles stand out as pivotal core scaffolds in medicinal development, exhibiting a diverse range of noteworthy biological activities (Scheme 1A). Therefore, the development of efficient protocols for the synthesis of these structures is greatly sought after and has been made impressive progress over the last decades. On the other hand, piperazine ranks as the third most utilized N-heterocycle in pharmaceutical drugs after pyridine and piperidine, and more than 60 drugs contain a piperazine ring. In this context, we envision that the piperazine-spirooxindoles are potentially valuable additions to the growing set of spirooxindoles being investigated in medicinal chemistry and could offer new chemical space in drug development. However, such structures are elusive, which have been poorly represented in commercial drugs and rarely utilized in library screening for drug discovery. This is mainly due to the lack of efficient methods to synthesize them. Thus, we believe that designing a general approach to access these piperazinespirooxindole frameworks, preferably with stereocontrol, could make a difference by boosting the interest in them from the pharmaceutical industry. Among the numerous synthetic strategies, the formal (n+1) cycloaddition of diazooxindoles is one of the most straightforward methods to access different types of spirooxindoles (Scheme 1B, top). One typical approach is the (2+1) cyclopropanation of diazooxindoles with olefins for the rapid construction of spirocyclopropyl oxindoles, and the asymmetric version has also been well-established. Besides, the (4+1) cycloaddition of diazooxindoles with 1,4-synthons has been emerging as a powerful tool for the synthesis of spirocylopentyl oxindoles. Quite a few elegant examples have been reported, in which vinyl ketenes/isocyanates (Ashfeld ), Danishefsky dienes ), βfunctionalized carbonyl compounds (Moody and Hu ) and 1,3,5-triazinanes (Sun ) proved to be potent 1,4-synthon partners. Among these (4+1) reactions, two ingenious asymmetric strategies have been developed. Ashfeld and Liu independently reported the enantioselective formal (4+1) cycloaddition of diazooxindoles with vinyl ketenes or Danishefsky dienes by using either Rh2(S-TCPTTL)4 or Rh2(R-PTTL)4 complex as the catalyst. This protocol involves an initial enantioselective (2+1) cyclopropanation to form vinylcyclopropanes (VCPs) followed by a subsequent stereoretentive 1,3-quaternary carbon migration. Hu described another asymmetric (4+1) cycloaddition of diazooxindoles with 2-mercaptoketones by using Rh2(OAc)4/chiral phosphoric acid (CPA) cooperative catalysis, which proceeds through CPA-assisted enantioselective intramolecular electrophilic trapping of the sulfonium ylide intermediate generated from diazooxindoles under rhodium catalysis. By using the same strategy, Hu further realized an asymmetric (5+1) cyclization of diazooxindoles with ohydroxymethyl chalcones through CPA-assisted enantioselective intramolecular Michael-type trapping of oxonium ylide derived from diazooxindoles under rhodium catalysis (Scheme 1B, bottom). Albeit with these achievements, there is still a strong need to develop general and convenient strategies of high order (n+1) (n > 4) cycloaddition of diazooxindoles for the rapid construction of novel spirooxindoles with larger rings.