Electrochemical synthesis and N-acylation of oxazolidin-2-ones: recent developments

A simple electrochemical method for the synthesis and N-acylation of chiral oxazolidin-2-ones (Evans’ chiral auxiliaries) is here described. It avoids the use of strong chemical bases, obtaining the deprotonating reagent by cathodic reduction of solutions of acetonitrile containing tetraethylammonium perchlorate as supporting electrolyte. This electrolysis is carried out inmild conditions and avoiding the use of toxic and harmful reagents, as phosgene and its derivatives, or drastic conditions of temperature and pressure, as requested in the classical chemical synthesis. The yields in oxazolidin-2-ones and N-acylated derivatives are good to high and, moreover, the reactionrequests a very simple work up.