NSF Career: Enamine-Metal Lewis Acid Bifunctional Catalysts for Asymmetric Organic Transformations

University Of North Texas, Denton TX

Investigators

Abstract

Professor Hong Wang of Miami University Oxford Campus is supported by the Chemical Catalysis (CAT) Program in the Division of Chemistry to develop bifunctional catalysts combining a metal center with an organocatalytic center on a single molecule for potential applications in asymmetric organic transformations. Bifunctional enamine-metal Lewis acid catalysts will be synthesized and used for asymmetric carbon-carbon and carbon-heteroatom bond forming reactions which cannot be achieved without the synergistic action of the two catalytic centers. Direct aldol condensations with ketones and inverse-electron-demand hetero-Diels-Alder reactions will be investigated. The catalyst design allows for the combination of different amine bases with different metals, which broadens the spectrum of applicability of these bifunctional catalytic systems to a wide range of organic reactions. The development of Lewis acid-Lewis base bifunctional systems is challenging because the acid and the base are prone to self-quenching and inactivation. The proposed research promises to circumvent this problem by judicious molecular architecture with sufficient flexibility to bring the organic base and the metal Lewis acid into close proximity but with enough rigidity and steric hindrance to prevent their binding. The proposed research could significantly impact asymmetric catalysis and the synthesis of fine chemicals and pharmaceuticals. The results will be integrated into a new graduate course in catalysis and an outreach plan will be implemented to provide summer research experience to minority undergraduate students and their teachers from Texas A&M University-Kingsville and to high school teachers from area high schools.