A Mannich/cyclization cascade process for the asymmetric synthesis of spirocyclic thioimidazolidineoxindoles

Chem Commun (Camb). 2014 Dec 7;50(94):14771-4. doi: 10.1039/c4cc06000h.

Abstract

An asymmetric cascade Mannich/cyclization reaction between 3-isothiocyanato oxindoles and sulfimides using a commercially available organocatalyst has been developed. A wide range of structurally diverse spiro[imidazolidine-4,3'-oxindole] derivatives were obtained with good yields (up to 92%) and excellent enantioselectivities (up to 99% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Oxindoles
  • Spiro Compounds / chemistry*

Substances

  • Indoles
  • Oxindoles
  • Spiro Compounds
  • 2-oxindole