Anion Cascade Reactions. Part I: Synthesis of 3-Isoquinuclidones from a Nazarov-like Reagent

A simple and atom-economical one-step protocol is described for the synthesis of biologically valuable 3-isoquinuclidones. The method proceeds from the simple starting materials, α-acyl N-arylcinnamamides, and can be performed under mild conditions in the presence of tBuOK. The key steps of this process are the double Michael addition reaction of a Nazarov-like reagent and the subsequent intramolecular hemiamination. These flexible intermolecular reactions could be performed on a gram scale.