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

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.

本研究报道了由3-溴氧化吲哚（3-bromooxindoles）原位生成的吲哚-2-酮与苯酚的有机催化不对称去芳构加成反应。该方法通过苯酚的去芳构化过程，在温和反应条件下高效构建了一系列带有相邻全碳季碳手性中心的对映富集型3,3'-二取代氧化吲哚类化合物。此外，代表性放大反应及去芳构化产物的相关转化，均证实了该反应策略具备可观的合成应用潜力。