In the course of a simple mechanistic study on the rearrangement of Zincke aldehydes to Z- α, β, γ, δ-unsaturated amides, a thermally induced pericyclic cascade rearrangement that converts Zincke aldehydes derived from allylic and homoallylic amines into polycyclic lactams was discovered. The key reaction involves an EZ alkene isomerization, a 6π electrocyclic ring closure, a [1, 5]-sigmatropic shift of hydrogen, a 6π electrocyclic ring- ...
