Assembly of spirooxindole derivatives containing four consecutive stereocenters by using cascade reactions catalyzed by an N-heterocyclic carbene

Chemistry. 2013 Apr 2;19(14):4428-31. doi: 10.1002/chem.201203436. Epub 2013 Mar 6.

Abstract

In-spiro-ational: Biologically important and synthetically challenging spirocyclopentaneoxindoles with four consecutive stereocenters, including one spiroquaternary stereocenter, have been constructed in good yields and diastereoselectivity by a cascade reaction catalyzed by an N-heterocyclic carbene (see scheme). This reaction also provides a new strategy to access highly unusual tricyclic oxindoles.

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Oxindoles
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Indoles
  • Oxindoles
  • Spiro Compounds
  • 2-oxindole
  • carbene
  • Methane