In Situ Generation of Cyclopentadienol Intermediates from 2,4-Dienals. Application to the Synthesis of Spirooxindoles via a Domino Polycyclization

Abstract

An efficient domino polycyclization combining different classes of pericyclic reactions leads to complex spiroxindoles under mild conditions. This domino process represents a rare example of an in situ formation of cyclopentadienol derivatives from an interrupted iso-Nazarov electrocyclization of 2,4-dienals and their use in [4 + 2] cycloaddition reactions. According to the reaction conditions, different polycyclic architectures are obtained in good yields and excellent diastereoselectivities.