In conclusion, we developed a simple and highly efficient synthetic methodology for the diastereoselective construction of multifunctionalized 3,3'-pyrrolidonyl-spirooxindoles in response to the demand for a new methodology for the construction of this scaffold. The mechanism underlying the preferential feasibility of regioselective cascade ring closure, where the reduced nitro group attacks the nitrile group while the ester groups remain inert throughout the reaction process, was investigated by DFT study. We are further pursuing efforts towards the application of densely functionalized Michael adducts with asymmetric version in our laboratory, as well as, expanding the strategy for new organic transformations.