Metal-containing Schiff base/sulfoxides were developed as chiral ligands for Pd(II)-catalyzed asymmetric intramolecular allylic C-H amination reactions. The use of metal-containing Schiff base ligands allows tuning the selectivity and reactivity of the Pd(II)-catalyst, whereby a Schiff base-Cu(II)/sulfoxide ligand in combination with Pd(OAc)(2) showed the best performance. Both internal and terminal alkenes were applicable, and the C-H amination products were obtained in up to 91:9 er