STEREOSELECTIVE SYNTHESIS OF VINYL IODIDES FROM VINYLBORONATE PINACOL ESTERS USING ICL

Polyenyl-1-boronic acids, with hindered pinacol esters, are difficult to transform into the corresponding Z or E-iodides under literature reaction conditions. However, reaction of trans-polyenyl-1-boronate pinacol esters with sodium methoxide, followed by monochloroiodide provides the corresponding E-iodides, while reaction with monochloroiodide, followed by sodium methoxide provides the corresponding Z-iodides.