Efforts to expand the scope and utility of the aza-[4+3] cycloaddition reaction of aza-allylic cations and dienes have led our group to explore its intramolecular variation. In these examples the alpha-halo amide and diene are tethered together and undergo an efficient cycloaddition reaction under basic conditions to provide polycyclic heterocyclic products. Details of the development, optimization and application in target-directed synthesis will be presented.

Development of intramolecular aza-[4+3] cycloaddition reactions and their applications in target-directed synthesis

243rd National Meeting (2012)

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