This thesis describes the catalytic asymmetric epoxidation of olefins mediated by
oxaziridinium salts. The introduction highlights some of the most successful methods
for preparing chiral oxiranes and hints at the synthetic utility of this versatile
molecule.
The second chapter is dedicated to our efforts to synthesize chiral iminium salts as
catalysts for asymmetric epoxidation. The first part of this chapter describes previous
Page group findings and leads on to the current author's efforts in this area. Initial
results from modified amino acids, cyclo-condensed to form dihydroisoquinolinium
salts, showed that an aromatic unit at C4 of our catalysts was vital for asymmetric
induction. Following this, several catalysts substituted at the 4-position of the
aromatic functionality were tested, and found to be effective mediators for asymmetric
epoxidation. Triphenylethylene was epoxidized with up to 71% ee when using oxone
as the stochieometric oxidant. [Continues.
