Solvent Effect in Gold(I)-Catalyzed Domino Reaction: Access to Furopyrans
Patrick Wagner1, Nayan Ghosh1, Vincent Gandon2,3
1Université de Strasbourg, CNRS, Laboratoire d'Innovation Thérapeutique, UMR 7200, 67000 Strasbourg, France.
Abstract:
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.
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