A novel cascade reaction involving oxidative dearomatization/semipinacol rearrangement of indol-2-yl cyclobutanols is explored with N-sulfonyloxaziridine (Davis oxaziridines) as oxidant, generating various 2-spiroquaternary 3-oxindoles in modest to good yields. This method might be useful in the synthesis of indole-based alkaloids bearing 2-spiroquaternary carbon centers. PTS=p-toluenesulfonic acid monohydrate.
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