Solvent Effect in Gold(I)-Catalyzed Domino Reaction: Access to Furopyrans - Archive ouverte HAL
Article Dans Une Revue Organic Letters Année : 2020

Solvent Effect in Gold(I)-Catalyzed Domino Reaction: Access to Furopyrans

Résumé

We report an efficient synthesis of furopyrans through a gold(I)-catalyzed domino reaction. Starting from the same source, and by changing the solvent of the reaction, two classes of furopyrans are accessible. During this one-step process, which takes place in DMF, two bonds and two heterocycles are formed. DFT calculations furnish the mechanistic understanding of this transformation. The sequence includes a 5-endo-dig cyclization, a regioselective 8-endo-dig cyclization, a retro 8p and a 6p electro-cyclization.

Domaines

Chimie
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Dates et versions

hal-02989311 , version 1 (09-11-2020)

Identifiants

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Patrick Wagner, Nayan Ghosh, Vincent Gandon, Gaëlle Blond. Solvent Effect in Gold(I)-Catalyzed Domino Reaction: Access to Furopyrans. Organic Letters, 2020, 22 (18), pp.7333-7337. ⟨10.1021/acs.orglett.0c02663⟩. ⟨hal-02989311⟩
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