Catalytic Enantioselective 1,3-Alkyl Shift in Alkyl Aryl Ethers: Efficient Synthesis of Optically Active 3,3'-Diaryloxindoles

Angew Chem Int Ed Engl. 2018 May 14;57(20):5735-5739. doi: 10.1002/anie.201801650. Epub 2018 Apr 20.

Abstract

Reported is the first organocatalytic asymmetric 1,3-alkyl shift in alkyl aryl ethers for the synthesis of chiral 3,3'-diaryloxindoles using a chiral Brønsted acid catalyst. Preliminary results showed that each enantiomer of the 3,3'-diaryloxindole, and a racemic mixture, showed different antiproliferative activities against HeLa cell lines by using an MTT assay.

Keywords: Brønsted acid; heterocycles; organocatalysis; rearrangements; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Ethers / chemistry*
  • HeLa Cells
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Oxindoles / chemical synthesis*
  • Oxindoles / chemistry
  • Oxindoles / pharmacology
  • Phosphoric Acids / chemistry*
  • Stereoisomerism

Substances

  • Ethers
  • Oxindoles
  • Phosphoric Acids
  • phosphoric acid