Electrochemical methods for the synthesis and the N-acryloylation of oxazolidin-2-ones chiral auxiliaries

Simple electrochemical methodologies for the synthesis (without the use of toxic and dangerous reagents) of chiral oxazolidin-2-ones by reaction of activated CO2 with chiral amino alcohols and for the N-acryloylation of oxazolidin-2-ones with activated α,α’- polychloroketones, have been reported. The activation of carbon dioxide was achieved either by electrochemical reduction of CO2 or by reduction of a gaseous mixture of O2/CO2 or by deprotonation of the substrates (via electrogenerated bases). The activation of polychloroketones was carried out by their electrochemical reduction in solutions containing oxazolidin-2-ones as well as ketones. Chiral oxazolidin-2-ones and N-enoyl oxazolidin-2-ones were isolated in good to high yields.