The direct functionalization of β-C(sp2)-H bonds in enamides has garnered increasing attention within the realm of organic synthesis. However, these remarkable advancements are predominantly dependent on transition metals; limited success has been achieved via organocatalytic catalysis. Herein, we report a CPA-catalyzed β-C(sp2)-H functionalization of enamides cascade intramolecular cyclization to synthesize the chiral dihydropyrimido[1,6-a]indoles bearing gem-difluoromethylene. Moreover, this methodology enables the synthesis of diverse chiral dihydropyrimido[1,6-a]indoles with outstanding enantioselectivities in moderate to high yields.