Part I: Designing strong chiral Bronsted acids and their application for the Aza-Henry reaction, and Part II: Syntheses of uracil derivatives

Part I: Designing strong chiral Bronsted acids and their application for the aza-Henry reaction. Nature uses chiral Bronsted acids catalytically for numerous organic reactions. Organic chemists have until only very recently realized the importance of this unique class of catalyst. As a result, there are very few known chiral Bronsted acids used in traditional asymmetric organic reactions. In recent years, due to the tremendous need for new asymmetric organic reactions in the pharmaceutical and food industries, interest in strong chiral Bronsted acids has been steadily growing. Currently, there are only a few of these acids known that have been used successfully for organic reactions. The research presented here involves exploration of a new class of chiral Bronsted acids for organic reactions. In addition, this research focuses on the importance of strong acidity as well as asymmetry for aza-Henry reaction. Binaphthyl sulfur-containing acid systems, which are analagous to sulfuric acid (H2SO4 ), were found to be especially attractive. This dissertation reports on the use of an innovative application of these asymmetric chiral sulfonate/sulfate systems in conjunction with a strong Bronsted acid. These new catalytic systems were very successful for obtaining asymmetry in the aza-Henry reaction.;Part II: Syntheses of uracil derivatives. 5-Aryl uracils are important building blocks for the synthesis of different nucleotides and nucleosides. Hossain had earlier reported an unprecedented reaction for 3-hydroxyaryl acrylate formation. The present research takes advantage of this innovation and further applies these 3-hydroxyaryl acrylates for the synthesis of 5-aryl uracils.