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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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024515
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 19, 2019 - 11:10:10 AM
Last modification on : Friday, October 9, 2020 - 9:50:59 AM

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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, American Chemical Society, 2018, 20 (3), pp.792-795. ⟨10.1021/acs.orglett.7b03934⟩. ⟨hal-02024515⟩

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