Highly congested epoxysulphones with stereoselectivity were synthesized from unsaturated sulphones. A comparison of diastereoselectivity has been made between the epoxysulphones synthesized using m-CPBA and H2O2. The synthesized compounds were characterized by using elemental analysis, IR, 1H-NMR and Mass spectral studies. The results indicate that m-CPBA epoxidations are sterically controlled and provide crude model for determination of the operation of hydrogen bonding in the reaction of H2O2 epoxidations. All these new compounds exhibited differential antibacterial and antifungal activities.