Chiral cyclopentadienyl (Cp) catalysts are an exceptional tool for inducing stereodivergent interactions between achiral molecules and transforming them into chiral substances with excellent enantiomeric purity. These essential interactions are a result of the geometrical arrangement of a chiral pocket modeled by a chiral Cp ligand that surrounds the central metal atom. Any alteration in ligand architecture is reflected in the overall stereoelectronic nature of the chiral Cp catalyst. Consequentially, the efficiency of a chiral catalyst is indivisible from the means of synthesis of a chiral ligand and the level of structural modularity that specific synthetic design allows. To reach the full potential of chiral Cp ligands, it is imperative to establish new fundamental principles and protocols that would bypass current synthetic limitations and simultaneously allow a high level of modification of structural features for a large number of molecular scaffolds. This interdisciplinary project offers an alternative means for the construction of chiral cyclopentadienyl ligands that interlinks a reliable existing methods and innovative solutions guided by the RESET (Reliability, Efficiency, Structural modification, Economy, Transferability) principles to address the current challenges imposed by lack of general synthetic approaches. Merging these principles with accumulated knowledge on stereoselective transition-metal catalysis will lead to improvement of existing Cp-ligand families, but also would set a firm platform on which potential breakthroughs in disparate catalytic transformations are expected.