The first enzymatic Achmatowicz reaction: selective laccase-catalyzed synthesis of 6-hydroxy-(2H)-pyran-3(6H)-ones and (2H)-pyran-2,5(6H)-diones

Abstract

The laccase-catalyzed oxidation of (5-alkylfuran-2-yl)carbinols using aerial oxygen as an oxidant selectively affords 6-hydroxy-(2H)-pyran-3(6H)-ones with yields up to 90%. With suitable substituted furan-2-yl carbinols as substrates the procedure allows the efficient preparation of (2H)-pyran-2,5(6H)-diones in a single step.