Face selective reduction of the exocyclic double bond in isatin derived spirocyclic lactones

Org Biomol Chem. 2013 Jan 14;11(2):244-7. doi: 10.1039/c2ob27008k. Epub 2012 Nov 19.

Abstract

We report an unusual face selective reduction of the exocyclic double bond in the α-methylene-γ-butyrolactone motif of spiro-oxindole systems. The spiro-oxindoles were assembled by an indium metal mediated Barbier-type reaction followed by an acid catalyzed lactonization.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Indium / chemistry
  • Isatin / chemistry*
  • Lactones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Oxidation-Reduction
  • Spiro Compounds / chemistry*

Substances

  • Lactones
  • Spiro Compounds
  • Indium
  • Isatin