Stereospecific cross-coupling reactions as a tool for three-dimensional molecular diversification

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PROJECT SUMMARY/ABSTRACT Using enantioenriched organometallic nucleophiles in palladium-catalyzed carbon-carbon bond- forming reactions, we aim to develop general tools for the rapid preparation of non-racemic biologically active molecules. By establishing the final stereogenic configuration prior to the formation of the final desired bond, the rapid preparation of diverse libraries of single- enantiomer drug candidates for use in biological assays will be achievable. The use of optically active secondary alkylboron and alkylstannane nucleophiles will initially be explored in Pd- catalyzed alkyl-aryl cross-coupling reactions, with particular focus on the derivatization of medicinally relevant organic frameworks. The inclusion of heterocycles will be emphasized in order to maximize access to chiral structural motifs that are currently inaccessible but are of biological or pharmaceutical interest.