A PPh3-catalyzed sequential cycloaddition of maleimides with unsaturated pyrazolones has been developed. This protocol provides a simple and practical strategy for the construction of dispirocyclopentyl-[dihydropyrazolone-pyrrolidinedione] pyrrolidinedione skeletons containing five contiguous stereogenic centers, including two spiro-quaternary centers, with moderate yields (34-73%) and excellent diastereoselectivities (>20 : 1).