An efficient electrochemical method for N-acryloylation of oxazolidin-2-one chiral auxiliaries with α,α′-di- and trichloroketones

A new synthesis of N-enoyloxazolidin-2-ones has been performed by electrochemical reduction of α,α′-di- and trichloroketones in aprotic solvent in the presence of Evans’ chiral auxiliaries (oxazolidin-2-ones). The electrochemical reduction of trichloroketones via a chlorocyclopropanone as intermediate allows a Favorskii rearrangement involving trichloroketones and oxazolidin-2-ones. N-Enoyloxazolidin-2-ones have been obtained this way under mild reaction conditions and in good to high yields.