Catalytic asymmetric [3+2] annulation of allylsilanes with isatins: Synthesis of spirooxindoles

Nadine V. Hanhan, Nicolas Ball-Jones, Ngon T. Tran, Annaliese K. Franz

Research output: Contribution to journalArticlepeer-review

97 Scopus citations

Abstract

Silyl-inspired spirocycle: The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl 2(SbF 6)/L catalyst and TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity at room temperature. The Si-C bond can be oxidized to deliver hydroxy-substituted spirooxindoles. TMS=trimethylsilyl.

Original languageEnglish (US)
Pages (from-to)989-992
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number4
DOIs
StatePublished - Jan 23 2012

Keywords

  • allylic compounds
  • annulation
  • asymmetric catalysis
  • enantioselectivity
  • scandium

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