A One-Pot Regiospecific Synthesis of Highly Functionalized 1,4-Benzodioxin Derivatives from an Electrochemically Induced Diels−Alder Reaction - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2005

A One-Pot Regiospecific Synthesis of Highly Functionalized 1,4-Benzodioxin Derivatives from an Electrochemically Induced Diels−Alder Reaction

Résumé

The anodic oxidation of pyrogallol derivatives produces chemically unstable o-quinone heterodienes, which are trapped in situ by enamine dienophiles through regiospecific inverse-electron-demand Diels-Alder reactions. The possibility of introducing variations in both cycloaddition partners gives rise to highly substituted 1,4-benzodioxin cycloadducts with up to five elements of diversity. The reactions proceed under mild conditions with a good efficiency. The methodology should be amenable to the assembly of libraries of biologically relevant heterocycles.
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Dates et versions

hal-02384997 , version 1 (27-11-2020)

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Daiwang Xu, Angèle Chiaroni, Martine Largeron. A One-Pot Regiospecific Synthesis of Highly Functionalized 1,4-Benzodioxin Derivatives from an Electrochemically Induced Diels−Alder Reaction. Organic Letters, 2005, 7 (23), pp.5273-5276. ⟨10.1021/ol052146e⟩. ⟨hal-02384997⟩
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