Five-membered ring nitrogen-containing heterocycles are privileged pharmacophores in the field of medicinal chemistry. These heterocyclic molecules are key scaffolds in several blockbuster drugs and natural products. Thus, there is a continuous demand for the development of more efficient and systematic methods to access them. We have found simple and inexpensive reaction conditions for the synthesis and isolation of a series of robust diaziridine synthons. This discovery allows us to explore their reactivity in transition-metal mediated diastereoselective dipolar cycloadditions to access a wide variety of stereochemically-dense heterocycles. The versatility of these synthetic building blocks, would allow the formation of complex heterocycles when reacting intramolecularly across the <i>N-C</i> bond and the alkenylether. This study would provide efficient and continuous access to complex highly functionalized heterocycles from simple scaffolds, which will facilitate the engineering of convergent approaches towards more complex heterocyclic pharmacophores.

Diastereoselective synthesis of complex heterocycles from the intramolecular cycloadditon of substituted alkenyldiaziridines

254th National Meeting (2017)

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