Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines

Giulia Rainoldi, Matteo Faltracco, Claudia Spatti, Alessandra Silvani*, Giordano Lesma

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review


This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented.

Original languageEnglish
Article number2016
Issue number11
Publication statusPublished - 1 Nov 2017


  • Azetidines
  • Cinchona-based catalysts
  • Organocatalysis
  • Spirooxindoles


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