Due to the ubiquity of allylic alcohols, the efficient installation of a hydroxyl group adjacent to doubly bonded carbons has garnered considerable attention. Kharasch and Sosnovsky’s allylic oxidation has been shown to yield an effective conversion, with recent examples attaining moderate to excellent e.e’s by employing chiral bis(oxazoline) ligands. Herein, we report the application of N-heterocyclic carbenes as ancillary ligands under these oxidative conditions. Achiral moieties have been synthesized and steps towards the synthesis of a chiral ligand are on going. Response surface methodology is currently being employed to model and optimize the NHC mediated oxidation by elucidating the effects of catalyst loading, time and temperature.

Designing catalytic N-heterocyclic carbene complexes for enantioselective allylic oxidation

249th National Meeting (2015)

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