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Many important problems remain to be solved in catalytic asymmetric epoxidation, despite substantial progress in the past three decades. We drew our inspirations from the reactivity of metalloenzymes such as cytochrome P-450 and vanadium haloperoxidase, which perform some of the most difficult chemical transformations. Through carefully designed ancillary ligands, we have achieved asymmetric epoxidation and related functionalizations on a broad scope of substrates to afford products that were previously difficult to access. This dissertation will include 1) iron-phenanthroline catalyzed asymmetric epoxidation of α, β-unsaturated esters; 2) tandem enantioselective epoxidation and ring-opening kinetic resolution for the synthesis of virtually enantiopure aminodiols; and 3) synthetic studies towards (+)-catharanthine.


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