Solvent Effect in Gold(I)-Catalyzed Domino Reaction: Access to Furopyrans
journal contributionposted on 01.09.2020 by Patrick Wagner, Nayan Ghosh, Vincent Gandon, Gaëlle Blond
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We report an efficient synthesis of furopyrans through a gold(I)-catalyzed domino reaction. By starting from the same source and 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, and a retro 8π and a 6π electrocyclization.