PHASE-TRANSFER CATALYZED ASYMMETRIC OXIDATION REACTIONS

Abstract

PHASE-TRANSFER CATALYSIS OFFERS A SIMPLE AND ROBUST METHOD FOR ASYMMETRIC OXIDATION REACTIONS. IN THIS STUDY, WE ARE INTERESTED IN EXPANDING THE SCOPE OF ASYMMETRIC PHASE-TRANSFER CATALYZED OXIDATION REACTIONS USING CHIRAL PHASE-TRANSFER CATALYSTS AND ENVIRONMENTALLY-BENIGN OXIDANTS.

IN THE FIRST PART OF THIS THESIS, A PHASE-TRANSFER CATALYZED ENANTIOSELECTIVE A-HYDROXYLATION REACTION OF KETONES WAS DEVELOPED. UTILIZING A DIMERIC PHASE-TRANSFER CATALYST IN TANDEM WITH MOLECULAR OXYGEN, WE SHOWED THAT BOTH ACYCLIC AND CYCLIC KETONES CAN BE HYDROXYLATED EFFICIENTLY TO YIELD TERTIARY A-HYDROXYKETONES WITH GOOD TO EXCELLENT ENANTIOSELECTIVITY.

IN THE SECOND PART OF THIS THESIS, THE ASYMMETRIC PHASE-TRANSFER CATALYZED EPOXIDATION OF NITROALKENES WAS EXPLORED. NEW BIFUNCTIONAL PHASE-TRANSFER CATALYSTS BASED ON THE CHIRAL 1-AMINO-2-INDANOL SCAFFOLD WAS DESIGNED, SYNTHESIZED AND APPLIED TO THE EPOXIDATION REACTION. PRELIMINARY RESULTS SHOWED THAT THE NEW BIFUNCTIONAL CATALYSTS LED TO BE