A palladium(II)-catalyzed enantioselective oxidative cross-coupling of ferrocenes with heteroarenes is described. Mono-N-protected amino acids can be used as sources of chirality. With azine as an efficient directing group, various substituted planar chiral ferrocenes were obtained via a dual C-H bond activation pathway in medium yields (up to 72%) with good enantioselectivity (up to 89.4:10.6 er) under mild conditions.