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

摘要

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.