Phenyl α-bromovinyl sulfone in cycloadditions with azomethine ylides: an unexpected facile aromatization of the cycloadducts into pyrroles

Phenyl α-bromovinyl sulfone reacts with glycine ester Schiff bases regioselectively in the presence of catalytic amounts of AgOAc and DBU yielding polysubstituted pyrrolidine cycloadducts. Utilization of excess DBU induces subsequent facile aromatization of the cycloadducts and affords 5-arylpyrrole-2-carboxylic acid esters in 39–85% yields in a single step.