Reactions catalyzed by small organic molecules through non-covalent interactions are emerging as powerful tools for the synthesis of valuable target molecules. Specifically, hydrogen bond donors (HBDs) are useful non-covalent catalysts able to interact with a variety of functional groups and operate in a number of transformations.  Boronate ureas have been identified as a new class of HBDs with enhanced reactivity due to the strategic placement of an internal Lewis acid. Specifically, in comparison to conventional ureas, boronate ureas benefit from lower catalyst loadings, reduced reaction times and access to unique reactivity patters.  To this end, we have discovered boronate ureas operate as catalysts for the activation of nitrocyclopropanes in nucleophilic ring-opening reactions giving rise to valuable nitro ester building blocks in good yield.  Details behind the development of boronate urea activation of nitrocyclopropanes, including mechanistic investigations and applications toward the synthesis of bioactive targets, will be presented.

Boronate urea catalyzed reactions of strained rings

243rd National Meeting (2012)

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