Transition-metal-catalyzed C-H functionalizations have emerged as complementary and powerful tools to access molecular complexity from widely available starting materials. Herein, we present a strategy for asymmetric intramolecular Pd(0)-catalyzed C-H functionalizations. The outlined reactivity is based on the cooperative effect between a chiral phosphorous ligand and a carboxylate base acting as a relay of chirality during the enantio-discriminating concerted metalation deprotonation step. This approach allows the enantioselective construction of a range of important semi-saturated chiral nitrogen-containing heterocycles such as indolines, tetrahydroquinolines, and dibenzazepinones.