The recognition of nitro groups by ureas through hydrogen bonding interactions has provided a remarkable platform for the development of new chemical transformations catalyzed by noncovalent organocatalysts. Urea-activation of nitrocyclopropane carboxylates is one particularly attractive new direction in hydrogen bond donor catalysis enabling the efficient preparation of highly functionalized organic building blocks. Recently, we have discovered boronate urea activation of nitrocyclopropane carboxylates in the presence of nitrones gives rise to formal [3+2] dipolar cycloadditions to afford the corresponding oxazine products in high yield. The development of this reaction system, including elements of the catalyst design and reaction scope, will be presented.

Formal [3+2] dipolar cycloaddition reactions of nitrocyclopropane carboxylates

245th National Meeting (2013)

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