3-isothiocyanato oxindoles serving as powerful and versatile precursors to structurally diverse dispirocyclic thiopyrrolidineoxindoles through a cascade Michael/cyclization process with amino-thiocarbamate catalysts

Chemistry. 2013 Apr 26;19(18):5551-6. doi: 10.1002/chem.201300206. Epub 2013 Mar 12.

Abstract

Cascading catalysis: 3-Isothiocyanato oxindoles act as powerful and versatile precursors for a range of structurally diverse dispirocyclic thiopyrrolidineoxindoles containing two spiro-quaternary and three contiguous stereogenic centers in quantitative yields with excellent disatereo- and enantioselectivities by only using 1 mol % amino-thiocarbamate catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Isothiocyanates / chemical synthesis*
  • Isothiocyanates / chemistry
  • Molecular Structure
  • Oxindoles
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism
  • Thiocarbamates / chemistry*

Substances

  • Heterocyclic Compounds, 4 or More Rings
  • Indoles
  • Isothiocyanates
  • Oxindoles
  • Spiro Compounds
  • Thiocarbamates
  • 2-oxindole