We report an efficient [3+2] cycloaddition protocol for the synthesis of pyrazolo[1,2-a]pyrazolones from Morita-Baylis-Hillman adducts and N,N’-cyclic azomethine imines. The R-BINOL chiral phosphoric acid was identified as the suitable catalyst for the reported cycloaddition protocol. Almost all MBH adducts regioselectively delivered 7-oxo-pyrazolo[1,2-a]pyrazoles at an efficient yield of 69–91 %. With exception, the MBH adducts derived from acrylonitrile deliver 5-oxo-pyrazolo[1,2-a]pyrazoles comparatively at a higher yield than the 7-oxo-pyrazolo[1,2-a]pyrazoles. The density functional theory (DFT) studies demonstrate that the reaction is thermodynamically more feasible in the presence of R-BINOL chiral phosphoric acid.