Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature

Org Lett. 2014 Feb 7;16(3):724-6. doi: 10.1021/ol403402h. Epub 2014 Jan 16.

Abstract

The first examples of gold-catalyzed cyclizations of diols and triols to the corresponding hetero- or spirocycles in an aqueous medium are presented. These reactions take place within nanomicelles, where the hydrophobic effect is operating, thereby driving the dehydrations, notwithstanding the surrounding water. By the addition of simple salts such as sodium chloride, reaction times and catalyst loadings can be significantly decreased.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alcohols / chemistry*
  • Catalysis
  • Cyclization
  • Gold / chemistry*
  • Micelles
  • Molecular Structure
  • Sodium Chloride / chemistry*
  • Temperature
  • Water / chemistry*

Substances

  • Alcohols
  • Micelles
  • Water
  • Sodium Chloride
  • Gold