Novel one-pot synthesis of diverse γ,δ-unsaturated β-ketoesters by thermal cascade reactions of diazodicarbonyl compounds and enol ethers: transformation into substituted 3,5-diketoesters

Abstract

Sequential Wolff rearrangement of α-diazo-β-ketoesters followed by trapping of the ketene intermediates with enol ethers generated a variety of γ,δ-unsaturated β-ketoesters. This method involves a novel thermal cascade reaction and allows the synthesis of γ,δ-unsaturated β-ketoesters with trans-stereochemistry under catalyst-free conditions. The synthesized compounds were further transformed into novel 3,5-diketoesters, which were used for the synthesis of naturally occurring 2-pyrone and 1-naphthoic acid ester.