There is an increasing necessity for the pharmaceutical industry to develop enantiomerically pure drugs. Up till now, production of enantiomerically pure molecules has been provided by harvesting them from plants or utilising homogeneous catalysis and biocatalysis. None of these methods are efficient means of production, and attention is now being directed towards heterogeneous enantioselective catalysis as the preferred technique. This is on account of the high product yield and ease of separation of catalyst from the reaction mixture. Over the past few decades, a great deal of research has been conducted into investigating the Ni catalysed hydrogenation of β-ketoesters and Pt catalysed hydrogenation of α-ketoesters. These are the most successful systems for enantioselective heterogeneous catalysis. However, they are unsuitable for industrial purposes due to the low thermal and mechanical stability of the modified surfaces. The main goal throughout this project has been the investigation of surface-confined covalent reactions. The motivation of this research is to develop enantioselective heterogeneous catalysis; covalent networks are believed to infer the necessary thermal and chemical stability required to chirally modify catalytic surfaces for docking interactions with reactant species. Covalent organic frameworks (COFs) on surfaces hold potential for a number of chemical applications, and not just in the field of heterogeneous catalysis; for example in areas such as molecular electronics and templating.