Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines

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

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

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
JournalMolecules
Volume22
Issue number11
DOIs
Publication statusPublished - 1 Nov 2017

Fingerprint

Spiro Compounds
Cinchona
induction
Isatin
catalysts
preparation
synthesis
products
Derivatives
Catalysts
oxindole
ketimine
azetidine

Keywords

  • Azetidines
  • Cinchona-based catalysts
  • Organocatalysis
  • Spirooxindoles

Cite this

Rainoldi, Giulia ; Faltracco, Matteo ; Spatti, Claudia ; Silvani, Alessandra ; Lesma, Giordano. / Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines. In: Molecules. 2017 ; Vol. 22, No. 11.
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Organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines. / Rainoldi, Giulia; Faltracco, Matteo; Spatti, Claudia; Silvani, Alessandra; Lesma, Giordano.

In: Molecules, Vol. 22, No. 11, 2016, 01.11.2017.

Research output: Contribution to JournalArticleAcademicpeer-review

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