Construction of Vicinal All-Carbon Quaternary Stereocenters Enabled by a Catalytic Asymmetric Dearomatization Reaction of beta-Naphthols with 3-Bromooxindoles

摘要

The organocatalyzed asymmetric dearomative addition of phenols to indol-2-ones generated in situ from 3-bromooxindoles was reported. This methodology leads to the efficient construction of a series of enantioenriched 3,3'-disubstituted oxindoles bearing vicinal all-carbon quaternary stereocenters via a dearomatization process of phenols under mild reaction conditions. Additionally, the representative large-scale reactions and related transformations of the dearomatized products reveal the potential synthetic utility of this protocol.