Complex polycyclic lactams from pericyclic cascade reactions of Zincke aldehydes

SE Steinhardt, CD Vanderwal

Index: Steinhardt, Sarah E.; Vanderwal, Christopher D. Journal of the American Chemical Society, 2009 , vol. 131, p. 7546 - 7547

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Citation Number: 28

Abstract

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- ...