Abstract
Part one of this thesis describes the catalytic activity of Schiff base ligands and vanadium towards the asymmetric epoxidation of allylic alcohols. Currently, the ligands used for the vanadium-catalyzed epoxidation are hydroxamic acids. However, vanadium catalyzed reactions employing Schiff bases as ligands have been reported by various groups. We investigated these Schiff base ligands for enantioselectivity of epoxidation reactions. While Schiff bases are an alternative to the use of hydroxamic acids, enantioselectivity using the former was no greater than 10% ee. Part two of this thesis describes the efforts towards the synthesis of an eight-membered carbocycle through a radical mediated cyclization/fragmentation pathway. Previous methods for the construction of eight-membered rings include olefin metathesis and transition-metal catalyzed cycloadditions. Molander1 has also formed eight-membered rings through various radical cascade reactions initiated by SmI2. Our efforts towards an eight-membered ring using SmI2 concentrated on a vinyl cyclopropane as a radical trap were unsuccessful.