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

Patrick WagnerNayan GhoshVincent Gandon Gaëlle Blond

Published in: Organic letters (2020)

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.

Keyphrases

density functional theory
room temperature
ionic liquid
molecular dynamics
electron transfer
molecular docking
solar cells
amino acid
crystal structure