Biocatalytic Conversion of Furans into Pyrrolinones Using a Class I Unspecific Peroxygenase

The biocatalytic conversion of furans and amines into 4-pyrrolin-2-ones can be achieved using the Class I Unspecific Peroxygenase artUPO. The reactions are broad in scope and typically operate in good yield, using a simple, easily scalable H₂O₂ driven protocol, in which exogenous enzyme cofactors are not required. All of these biotransformations were performed on a preparative scale to deliver synthetically useful quantities of pyrrolinones. A cascade mechanism likely operates, in which UPO-mediated oxidative ring opening of the furan first delivers a reactive 1,4-dicarbonyl intermediate, followed by condensation with the added amine and rearrangement to the pyrrolinone product outside the UPO active site.