The Steglich Rearrangement of 2-Oxindole Derivatives Promoted by Anion-based Nucleophilic Catalysis

Cristina Trujillo, Mili Litvajova, Sarah A. Cronin, Ryan Craig, Stephen J. Connon

Research output: Contribution to journalArticlepeer-review

Abstract

The first small anion-triggered Steglich rearrangements are reported. Tetrabutylammonium carboxylates-, cyanide- and fluoride promote the O- to C-acyl transfer of a range of O-acylated oxindoles to form 3,3-disubstituted oxindole products with new quaternary stereocentres. DFT calculations on the TBAF-mediated reaction strongly support a nucleophilic catalysis mechanism involving initial attack of fluoride on the O-acyl group to give an enolate and an acyl fluoride in the rate determining step.

Original languageEnglish
Pages (from-to)3776-3780
Number of pages5
JournalChemCatChem
Volume11
Issue number16
Early online date31 May 2019
DOIs
Publication statusPublished - 21 Aug 2019

Keywords

  • catalysis
  • DFT
  • fluoride
  • oxindoles
  • Steglich rearrangement

Fingerprint

Dive into the research topics of 'The Steglich Rearrangement of 2-Oxindole Derivatives Promoted by Anion-based Nucleophilic Catalysis'. Together they form a unique fingerprint.

Cite this