Intramolecular Prins Reactions of Vinylcyclopropanes with Aldehydes and Ketones: A New Synthesis of Semicyclic Conjugated Dienes

Abstract

Carbonyl compounds bearing pendant vinylcyclopropanes react with sulfonic acids to produce semicyclic conjugated dienes. These functionalized dienes can be readily elaborated into complex polycyclic compounds.

Key words

vinylcyclopropane - cyclizations - ring opening - eliminations - conjugated diene

References

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5

The use of methanesulfonic acid in the reaction with 1 produced the corresponding mesylate in 48% yield.