An N-heterocyclic carbene (NHC) catalyzed asymmetric [3 + 3] annulation of α-bromoenals with 5-aminopyrazoles is described. Using the established methodology, a structurally diverse set of high value dihydropyrazolo[3,4-b]pyridine-6ones were efficiently constructed in high yields (up to 99%) with excellent enantioselectivities (up to > 99%). The easily available starting materials, broad substrate scope, mild reaction conditions, excellent yield and enantioselectivity make this strategy attractive for the asymmetric construction of pyrazolo-fused pyridone derivatives.