The study of intramolecular anodic olefin coupling reactions arising from diene substrates having an allylic alkoxy group have been studied. In all cases, the coupling reactions proceeded smoothly without elimination of the allylic alkoxy group. In addition, the reactions were found to afford five-membered ring products in a diastereoselective fashion. Substrates having both cis- and trans-disubstituted allyl silane olefin participants led to different ratios of products indicating that the cyclization reactions were under kinetic control.