Desymmetrisation of silylcyclopenta-2,4-diene was carried out by an asymmetric copper(I)-mediated cyclopropanation. An in-depth investigation with various ligands led to the discovery that the PyBox ligands 10a-c were the most efficient ligands for this transformation and led to the cyclopropane 7a with an ee of up to 72%. Further studies aimed at providing insights into the origin of this enantiocontrol are also provided.