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A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones.
RSC Adv
February 2021
Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology Wuhan 430070 China
CsOH·HO-catalyzed formal [3 + 3] cycloadditions of allenyl imide with β-ketoesters, 1,3-diketones or β-ketonitriles for the synthesis of tetrasubstituted 2-pyrone derivatives have been demonstrated. The allenyl imide was utilized as a C3-synthon, and a ketenyl intermediate was proposed the process of 1,4-addition of carbon anion to allene followed by elimination of the 2-oxazolidinyl group.
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