8 pi Electrocyclic Reaction of Phosphonate Derivatives: Access to Seven-Membered Cross-Conjugated Cyclic Trienes

An anionic 8 pi electrocyclic reaction of 4-(diethoxyphosphoryl)-1,3,6-heptatriene derivatives was developed. Under the influence of a base, the substrate underwent deprotonation at the C5 position followed by the 8 pi electrocyclization of the resulting heptatrienyl anion. The subsequent Horner-Wadsworth-Emmons reaction in one pot, following the addition of an aldehyde, resulted in the production of the 3-alkylidene1,4-cycloheptadiene derivative. The electrocyclic reaction proceeded in a stereospecific manner, resulting in the stereocontrolled formation of two neighboring stereogenic centers.