PhIO-Mediated Oxidative C=C Bond Cleavage and Reassembly toward Highly Functionalized Oxazolones

An efficient PhIO-mediated oxidative C=C bond cleavage and reassembly of enaminone toward oxazolone with high regioselectivity has been reported. DFT calculations revealed that the reaction proceeded through an oxygen atom transfer, C=C bond cleavage, alkylthio migration, and reassembly cascade. This strategy is highlighted by high atom and step economy with formation of five bonds in one pot and generation of a highvalued oxazolone skeleton under mild conditions.

Automated summary

An efficient and highly regioselective reaction method has been reported for the transformation of enaminone to oxazolone via PhIO-mediated oxidation and reassembly. DFT calculations revealed the mechanism and steps of the reaction, which demonstrates high atom and step economy and the ability to form a valuable oxazolone skeleton under mild conditions.