This lecture will describe our research over the last two decades, wherein we have attempted to develop low-molecular weight peptides as catalysts for asymmetric reactions. Over time, our view of asymmetry has ebbed and flowed, with foci on enantioselectivity, site-selectivity and chemoselectivity. So too, our perspective on complexity has evolved. In fact, complexity is a relative term that is often used to describe features of molecules that contain multiple functional groups or which exhibit difficult-to-control dynamics. As such, the goal of discovery of catalysts that perform selective reactions on complex substrates presents something of a moving target. We have often initiated experiments with moderate-complexity model systems. These studies have often been followed up by related explorations with complex natural products as substrates. These programs have provided an intriguing opportunity to think about the intersection of natural products chemistry and enzymology. Natural products have provided perennial inspiration for the development of synthetic methods. In parallel, enzymes have provided an analogous platform for the study of catalysis and for the conception of new catalysts. This lecture will recount an interplay of experiments stimulated by these two major classes of naturally occurring substances – natural products and enzymes – as we have endeavored to find catalysts that mediate selective bond-forming reactions on complex molecules.

<b>Award Address </b>(ACS Award for Creative Work in Synthetic Organic Chemistry sponsored by Aldrich Chemical Company, LLC). Searching for selective catalytic reactions in complex molecular environments

251st National Meeting (2016)

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Award Address (ACS Award for Creative Work in Synthetic Organic Chemistry sponsored by Aldrich Chemical Company, LLC). Searching for selective catalytic reactions in complex molecular environments