STEREOSELECTIVE SYNTHESIS OF VINYL IODIDES FROM VINYLBORONATE PINACOLESTERS USING ICI

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