Bispirooxindole derivatives containing three stereocenters, including two spiro quaternary centers, were synthesized in a high-yielding, atypically rapid, and stereocontrolled cascade Michael–cyclization reaction between methyleneindolinones and isothiocyanato oxindoles catalyzed by a bi- or multifunctional organocatalyst. Mild conditions were used to construct bispirooxindoles with excellent enantio- and diastereomeric purities within less than 1 min. Catalyst reconfiguration offered access to the opposite enantiomer. This exceptionally highly efficient procedure will allow diversity-oriented syntheses of this intriguing class of compounds with potential biological activities.
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