The synthesis and application of ferrocene-based palladacycles has been at the forefront of catalysis for a number of years. The use of C-H activation to synthesise such compounds has been a relatively new development. The work within this thesis attempts to develop on known protocols devised by Richards et al. for the generation of enantio-enriched planar chiral palladacycles. The first of which includes the synthesis and application of symmetrical and non-symmetrical phosphines, and in this work the latter have been transformed into a diastereomerically pure enantiomerically enriched palladacycle via a transcyclopalladation (Scheme I). Compound 343 was generated as a diastereomerically pure palladacycle in 96% ee, and the kinetic resolution of the phosphine pre-courser to 319 afforded a d.r. of 99:1 and a 76% ee. Finally, methods developed by Shu Li-You and Wu have been extended to a cobalt sandwich complex affording novel bi-substituted ligands (Scheme II).