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Updated: May 15, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Highly efficient enantioselective construction of bispirooxindoles containing three stereocenters through an
Hao Wu1, Li-Li Zhang, Zhi-Qing Tian
1State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071, PR China.
Abstract:
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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