The reaction between a nucleophile and an electrophile constitutes one of the most fundamental pathways underlying an extremely broad range of reactions in organic synthesis. Since the electrophile and the nucleophile can be activated by an acid and a base, respectively, a chiral acid, a chiral base, or a bifunctional molecule can, in principle, promote an enantioselective nucleophile-electrophile reaction. This project is focused on the development of effective bifunctional organocatalysts for promoting enantioselective organic reactions. New bifunctional organocatalysts for asymmetric organic reactions, incorporating amine/phosphine/phosphine oxide (bases) and sulfonamides/(thio)ureas (acids) will be prepared. The ability of these compounds to catalyze a variety of organic reactions will be explored, including asymmetric Morita-Baylis-Hillman reactions, nucleophilic addition of trimethylsilyl cyanide and trimethylsilyl azide to aldehydes, ketones, and Schiff bases, and Michael addition of trimethylsilyl cyanide and trimethylsilyl azide to nitroolefins and alpha, beta-unsaturated carboxylic acid derivatives.
With the support of this award from the Organic and Macromolecular Chemistry Program, Professor Wei Wang, of the Department of Chemistry at the University of New Mexico, is developing new methods to catalyze selective and efficient organic reactions. Small organic molecule-based catalysis (termed organocatalysis) has emerged as a powerful new tool in asymmetric synthesis, but this field remains in its infancy. Professor Wang and his students are exploring the design, synthesis, and applications of organocatalysts that bring two complementary types of reactivity to bear on a single substrate. These unique catalysts have the capacity to activate new types of substrates, thus creating new and efficient organic reactions for the transformation of simple compounds into more complex structures. These reactions, which are expected to be of general applicability in the synthesis of pharmaceuticals and other organic products, illustrate many of the principles of green chemistry, offering the potential for selective syntheses under environmentally benign conditions.
