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

Author: Khalili Gholamhossein  

Publisher: Taylor & Francis Ltd

ISSN: 1741-5993

Source: Journal of Sulfur Chemistry, Vol.34, Iss.5, 2013-10, pp. : 532-538

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Abstract

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.

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