Reaction of 2-Aroylmethylenemalonates with Corey Ylide

The reactions of 2-aroylmethylenemalonates with Corey ylide were studied. Corey ylide, prepared in-situ from 1.0 equiv. of trimethylsulfoxonium iodide and 2.5 equiv. of sodium hydride in N,N-dimethylformamide (DMF), reacted with 2-aroylmethylenemalonates at -23 degrees C via a conjugate addition/elimination sequence to give 2-(1-aroylvinyl)malonates. Corey ylide, prepared in-situ from 2.2 equiv of trimethylsulfoxonium iodide and 5.0 equiv. of sodium hydride in DMF, reacted with 2-aroylmethylenemalonates at -23 to degrees C by a conjugate addition/elimination/conjugate addition/cyclopropanation sequence to give 2-(1-aroylcyclopropyl)malonates. Corey ylide, prepared in-situ from 1.1 equiv. of trimethylsulfoxonium iodide and 5.0 equiv. of potassium carbonate in DMF, reacted with 2-aroylmethylenemalonates at 0 degrees C via a conjugate addition/cyclopropanation sequence to give 2-aroyl-1,1-cyclopropanedicarboxylates. These three processes can be controlled with high chemoselectivity by simply adjusting the base, the reagent ratios and the reaction temperature.