Synthesis of Diastereomeric Hydrobenzofurans and Hydronaphthofurans via an Iodine Reagent-Promoted Intramolecular Dearomatization Reaction

The first metal- and base-free construction of diastereomeric hydrobenzofurans and hydronaphthofurans, which were capable of further transformations to achieve natural product frameworks, was achieved by the intramolecular oxidized dearomatization of phenol or naphthol derivatives via the promotion of iodine reagents. Enantioselective products were obtained through chiral substrates or iodine catalysts. This step-economical protocol built multiple chiral centers with extensive tolerance of various substrates, which resulted in a potential molecular library for developing functional polycyclic scaffolds.