Formation of γ-Oxoacids and 1<i>H</i>-Pyrrol-2(5<i>H</i>)-ones from α,β-Unsaturated Ketones and Ethyl Nitroacetate

Michael addition of ethyl nitroacetate on α,β-unsaturated ketones followed by Nef oxidation under hydrolytic conditions yields γ-oxoacids instead of the corresponding α,δ-dioxoesters. A concerted decarboxylation step is proposed on the basis of computational results. Finally, conversion of the γ-ketoacids thus prepared into 1H-pyrrol-2(5H)-ones by reaction with primary amines under Paal−Knorr conditions is also reported.