Stereospecific Synthesis of Symmetrical Conjugated Dienes with Alkenylcopper Intermediates from Alkenyldialkylboranes

Article abstract of DOI:10.1021/jo01291a045

Sodium methoxyalkenyldialkylborates, obtained in the simple treatment of alkenyldialkylboranes with sodium methoxide, react readily with cuprous bromide-methyl sulfide at 0 deg C to afford symmetrical conjugated dienes.The dienes are formed with retention of configuration predetermined from the stereochemistry of the initial alkenylborane intermediate.