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

A.-S. Marques (1) , J. Marrot (1) , Isabelle Chataigner (2) , V. Coeffard (3) , G. Vincent (4) , X. Moreau (1)

1 ILV - Institut Lavoisier de Versailles
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
3 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
4 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay

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.

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry

A.-S. Marques, J. Marrot, Isabelle Chataigner, V. Coeffard, G. Vincent, et al.. In Situ Generation of Cyclopentadienol Intermediates from 2,4-Dienals. Application to the Synthesis of Spirooxindoles via a Domino Polycyclization. Organic Letters, 2018, 20 (3), pp.792-795. ⟨10.1021/acs.orglett.7b03934⟩. ⟨hal-02024515⟩