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Heterocyclic molecules are commonly found in both medicinal and material applications. Due to increasing demands for more efficient routes to known heterocycles and discoveries of new heterocycles, the design of innovative methods that facilitate access to these important scaffolds are required.

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To streamline the synthesis of heterocyclic and heteroatom-rich molecules, our laboratory has pursued the development of novel transformations that employ nitrone and hydroxylamine intermediates. We have discovered divergent conditions to unlock and control the reactivity embedded in the N–O bond of these compounds to achieve a diverse array of new reactions and efficiently prepare challenging C–O, C–N, and C–C bonds from simple starting materials. We have also developed complementary modular methods for generating nitrone and hydroxylamine rearrangement precursors using the Chan-Lam-Evans reaction and conjugate addition strategies.

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The general strategy described above has guided the synthetic studies described in the diagram below.

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Our current research efforts are focused on:

1. Expanding our repertoire of rearrangement reactions of nitrones and hydroxyl amines for the synthesis of new and challenging heterocyclic compounds.
2. Advancing our methods by creating asymmetric variants and exploring divergent pathways accessible with catalysis.
3. Studying the mechanism of the chemoselectivity of the C–N, and C–O bond forming processes discovered in our laboratory.
4. Applying our methods to medicinal chemistry applications with collaborations established through the UICentre for Drug Discovery.

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If you are an undergraduate student considering research opportunities in synthetic chemistry or a first-year graduate student considering joining a synthetic organic research lab, check out the link below to a short movie about day-to-day research activities in our lab.

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