One-pot synthesis of multi-substituted 4-pyrones by a gold-catalyzed cascade of Wolff rearrangement/[4+2]cycloaddition/elimination reactions

Abstract

An efficient one-pot method is described for the synthesis of a variety of di- and trisubstituted 4-pyrones based on the gold-catalyzed cascade reactions between cyclic or acyclic diazodicarbonyl compounds and vinyl ethers. The key strategy used involves the gold-catalyzed Wolff rearrangement of diazo compounds followed by [4+2] cycloaddition and elimination. This methodology is also applied to the synthesis of tetrasubstituted 4-pyrones. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.