Asymmetric epoxidation and dihydroxylation have been studied over decades using transition metals and chiral ligands. This research focused on... Show moreAsymmetric epoxidation and dihydroxylation have been studied over decades using transition metals and chiral ligands. This research focused on metal free, hydrogen-bonding activation of the oxidant, such as hydrogen peroxide. In order to activate hydrogen peroxide, different types of catalysts, including BINOLs, calixarenes and carboxylic acids were synthesized, characterized and tested. The activity tests showed that carboxylic acids were able to activate hydrogen peroxide and alkyl hydroperoxides to give epoxides and diols as products. Various carboxylic acids, such as commercial available achiral and chiral carboxylic acids, dicarboxylic acids, as well as synthesized trans- and cis-dicarboxylic acid, were tested with different substrates to maximize the yield and enantioselectivity. A current reaction system uses 10 mol % catalyst, no solvent and provides the epoxide with 70% yield and 60% ee over 24 hours. M.S. in Chemisty, December 2011 Show less
