Reaction of different α-sulfonyl acetamides with methyl acrylate

The base-induced tandem-coupling/cyclization reactions of various α-sulfonyl acetamide derivatives with methyl acrylate differentiated between two different pathways to form α-sulfonyl analogs of glutarimides and 2-hydroxycyclohexenecarboxylic acid derivatives in different ratios. The reaction of α-sulfonyl acetamide dianion with methyl acrylate depended on three factors: the stability of the dianion, concentration of methyl acrylate and the structure of sufonyl and amide substituents. By changing the reaction conditions, we efficiently controlled the cycloaddition reaction to synthesize the desired product, each of which has potential biological activities. A ring closure mechanism is proposed for the reactions.