Stereoselective synthesis of substituted arylsulfonylated 1,3-butadienes and 2-propenoates by sulfonylation of acetylenic ester

Protonation of the reactive intermediates produced in the reaction between sodium arylsulfinates and two equiv. of dialkyl acetylenedicarboxylates in DMF, by H₂O lead to substituted (1E,3E)-1-(arylsulfonyl)-1,3-butadiene-1,2,3,4-tetracarboxylates in moderate yields. A regioselective method for the synthesis of alkyl (E)-3-(arylsulfonyl)-2-propenoates is described. These reactions provide a useful synthetic route to highly functionalized 1,3-butadienes and 2-propenoates.