New Methodologies for the Synthesis of Aminoboronic Acids and Tetrahydroquinolines

There has been a rising interest in aminoboronic acids since their medicinal properties have been realized. Thus, new strategies for the synthesis of α- and β-aminoboronic acids would enable the discovery of bioactive molecules. Tetrahydroquinolines are also privileged scaffolds that are commonly found in natural products and therapeutically relevant molecules. This thesis reports the use of amphoteric boron carbonyl reagents in the synthesis of α- and β-aminoboronic acids. Following the introduction, Chapter 2 discusses the development of the Ugi four-component reaction with α-boryl isocyanide to furnish peptidomimetic α-aminoboronic acids. These molecules were shown to be bioactive against human caseinolytic protease P. In Chapter 3, the preparation of various β-aminoboronic acids from α-boryl aldehydes is described such as boryl enamide synthesis, boryl-Strecker reaction and an Ugi/aza-Wittig multicomponent reaction. The boryl enamides were highly useful synthetic intermediates and enabled the construction of tetracyclic lactams. The β-aminocyano(MIDA)boronates generated from the boryl-Strecker reaction were found to be potent and selective inhibitors of serine hydrolase α/β-hydrolase domain 3. Lastly, Chapter 4 presents a novel strategy for the synthesis of Povarov-type products using photocatalysis.Ph.D