The synthesis of chiral gem-difluorinated spiro-heterocyclic compounds continues to be a significant challenge in organic chemistry due to their widespread applications across various fields. Therefore, efficient asymmetric approaches for the synthesis of gem-difluorinated spiroindanone-dihydroquinazolinones are particularly valuable, especially in the industrial manufacturing of chiral fluorinated drugs. Herein, we developed the CPA-catalyzed asymmetric enantioselective cyclization reactions of gem-difluoroalkyl 1,3-indandiones with anthranilamides to achieve various chiral 2,2-difluoro-spiroindanone-dihydroquinazolinones in good to high yields with excellent enantioselectivities. Moreover, the mechanism experiment proved that the gem-difluoro substitution pattern promotes the reaction.