As per our best knowledge, an innovative approach for the diastereoselective synthesis of 3,3'-pyrrolidinyl spirooxindole, accomplished solely by one-pot sequential nitro-Michael addition reaction followed by partial reduction cyclization cascade to offers multifunctionalized 3,3'-pyrrolidinyl-spirooxindoles as well as DFT study for this type of regioselective cyclization has been not studied and reported so far.