An unprecedented tandem oxidation/Michael/aldol reaction is reported. The diastereoselective formation of only a single isomer of dispirocyclopentanebisoxindole and dispiro[acenaphthylene-1,1'-cyclopentane-3',1''-acenaphthylene]-2,2''dione is presented. The reaction generates two new C-C bonds and two all-carbon quaternary chiral stereocenters in a single step.
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