Methods for Selective Organic Synthesis based on Ionic Catalysts

Project Summary The major goal of this research program is to develop catalytic enantioselective transformations based on transition metal and chiral anion catalysis that will be broadly applicable to the preparation of therapeutically relevant organic molecules. Towards this end, new reactions for the enantioselective construction of C-O, C-N and C-halogen bonds are proposed. Particular emphasis is placed on the development of methods for the selective introduction of fluorine and fluorine-containing functional groups. Additionally, reactions that generate or employ available building blocks, such as alkenes and boronic acids, will be targeted. These methods will leverage new catalyst platforms, based on gold(III) complexes and phosphoric acid-based chiral anions, for the construction of fluorinated building blocks and heterocycles Additionally, the mechanistic underpinnings of these reactions will be studied, with a focus on uncovering the role of non-covalent interactions in achieving selectivity. Thus, we anticipate that this program will provide synthetic chemists and biomedical researchers with additional tools (reactions, catalysts, ligands etc.) for molecular synthesis and for single enantiomer construction, as well as provide principles for further development and application.