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Iron-Mediated Domino Interrupted Iso-Nazarov/Dearomative (3 + 2)-Cycloaddition of Electrophilic Indoles

Abstract : An efficient domino reaction combining different classes of pericyclic reactions leads to chiral complex polycyclic indoline-based architectures from achiral starting materials under mild conditions. This practical method is based on the ability of iron(III) chloride to promote both 4π electrocyclizations of 2,4-dienals and the C2–C3 umpolung of N-acetylindoles during the dearomative (3 + 2) cycloadditions.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046225
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:37:00 PM
Last modification on : Friday, October 9, 2020 - 9:50:59 AM

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A.-S. Marques, V. Coeffard, Isabelle Chataigner, G. Vincent, X. Moreau. Iron-Mediated Domino Interrupted Iso-Nazarov/Dearomative (3 + 2)-Cycloaddition of Electrophilic Indoles. Organic Letters, American Chemical Society, 2016, 18 (20), pp.5296-5299. ⟨10.1021/acs.orglett.6b02613⟩. ⟨hal-02046225⟩

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