A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones.

ABSTRACT

CsOH·H2O-catalyzed formal [3 + 3] cycloadditions of allenyl imide with ß-ketoesters, 1,3-diketones or ß-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 via the process of 1,4-addition of carbon anion to allene followed by elimination of the 2-oxazolidinyl group.