Abstract
An anionic 8π 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 8π 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-alkylidene-1,4-cycloheptadiene derivative. The electrocyclic reaction proceeded in a stereospecific manner, resulting in the stereocontrolled formation of two neighboring stereogenic centers.
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