Construction of Conformationally Restricted Bicyclic Lactam-Lactones by sp3 C-H Oxygenation


Victoria Shearer

Faculty Mentor(s)

Timothy Beng (Chemistry)


Climate change is a daunting predicament the world has found itself in, leading to an increase in green chemistry. A green chemistry technique that utilizes C-H bond activation is desirable. Due to this, a sustainable, cost-effective, and selective carbon-oxygen bond-forming lactonization (production of a cyclic ester) using amido acids was sought after. The conversion of a sp3 C-H bond of a lactam to a new C-O bond was done under mild (green) reaction conditions by using N-iodosuccinimide rather than a transition metal. Such a synthesis of conformationally constrained [3-2-1] bicyclic lactam-lactones is of great importance to pharmaceutical companies since they have beneficial biological activities. It is anticipated that this novel discovery would impact the arena of complex molecule synthesis in which late-stage oxygenation is often desirable. The motivation comes from observations that nitrogen and oxygen-containing heterocycles found in a broad range of products ranging from feedstock to pharmaceuticals. The only byproduct of this experiment will be hydrogen gas specifically, which in turn will be collected and used as a clean fuel that is not harmful to the environment.



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