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

13 November 2020

Org. Lett. (2020) https://doi.org/10.1021/acs.orglett.0c02663

Patrick Wagner ; Dr.  Nayan Ghosh ; Pr. Vincent Gandon ; Dr. Gaëlle Blond 

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.

 Org. Lett. (2020) https://doi.org/10.1021/acs.orglett.0c02663