An efficient and practical organocatalytic asymmetric [3 + 2] cycloaddition of difluoromethylated ketoimines and Pyrazolone derivatives catalyzed by quinine-derived thiourea has been disclosed. Under mild conditions, a broad range of CF2H-containing dispiro[benzo[b]thiophene-pyrrolidine-pyrazole]s bearing four adjacent chiral centers including two vicinal spiro quaternary stereocenters were obtained in good yields (66–96% yield) with moderate to excellent diastereoselectivities (82:18–95:5 dr) and enantioselectivities (70–98% ee).