Synthesis of Optically Active 1,3-Dienes from Alkenylstannanes by a Combination of Electro-Oxidation and Copper-Mediated Homocoupling Reaction.

The copper(II) salt mediated reaction of alkenylstannanes was reported to provide high stereospecificity for the homocoupling reaction to symmetrical dienes, though it required at least a stoichiometric amount of copper salt.1 Because of its highly stereoselective nature, we refined the copper-mediated coupling reaction of alkenylstannanes using electro-oxidation; the stereocontrolled synthesis of optically active diene 2 from alkenylstannane 1 was accomplished using catalytic amounts of Cu(II)C12 in combination with electro-oxidation (Eq. 1).2