The study of cycloaddition reactions between cyclopenta-1,3-diene and benzyl-acrylate, as well as benzyl-2-fluoroacrylate with and without the catalyst (TiCl4), was conducted using MEDT. The results of the energy profiles suggest that these reactions are stereoselective, meaning that they favor the formation of certain stereoisomers over others. Furthermore, the addition of TiCl4 as a catalyst appears to enhance the selectivity of these reactions, which is in line with experimental observations. Additionally, a docking study was carried out to predict the effect of stereochemistry and the presence of specific atoms, such as fluorine, on their ability to bind to viral proteins responsible for SARS-Covid-19 and HIV. Moreover, the notable affinity of Ligand 4 for HIV renders it a pivotal contender for extended research, possibly paving the way for enhanced antiretroviral drugs. Similarly, the encouraging affinity demonstrated by Ligand 1 towards the Covid-19 protein highlights its promise for Covid-19 drug development.