Amphoteric Molecules: from Reaction Discovery to Applications in Synthesis

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Our research program aims at the development and synthetic application of amphoteric reagents. As part of our efforts, we will be pursuing the chemistry of molecules that contain counterintuitive combinations of nucleophilic and electrophilic reaction centers. The bifunctional nature arising from "forced orthogonality" enables amphoteric molecules to participate in reactions of high atom- and step- economy. The capacity of these molecules to engage in multicomponent, cascade, and tandem processes makes them ideal tools for reaction discovery, medicinal chemistry, and green technology. Over the next 5 years, we will create a sophisticated portfolio of amphoteric reactivity, seeking applications that will range from fundamentally significant chemical transformations to understanding the properties of target molecules under consideration. These investigations will enable a wide range of academic and industrial researchers to run novel multicomponent processes using a growing collection of amphoteric molecules, explore the reactivity of "borointermediates" (molecules equipped with well-known functional groups in which a selected carbon atom(s) has been replaced by boron), and develop medicinal chemistry applications using our discoveries. Our studies will have practical significance and will be of broad applicability to pharmaceutical manufacturing because we will commercialize and market all synthetically useful reagents resulting from our efforts. In order to do this, we will take full advantage of our existing relationship with Sigma Aldrich. Our ties with the pharmaceutical industry, exemplified by active research collaborations with Merck, Pfizer, AstraZeneca, and GlaxoSmithKline will serve as a powerful platform to translate our research findings to a diverse range of Canadian stakeholders.