Anodic cyclization reactions: reversing the polarity of ketene dithioacetal groups

Org Lett. 2001 May 31;3(11):1729-32. doi: 10.1021/ol015925d.

Abstract

Intramolecular coupling reactions of ketene dithioacetal groups with enol ether and alcohol nucleophiles have been studied. The reactions were initiated by an anodic oxidation of the ketene dithioacetal and proved to be compatible with the formation of five- or six-member rings, as well as the stereoselective generation of quaternary carbons.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Cyclization
  • Ketones / chemical synthesis*
  • Oxidation-Reduction
  • Stereoisomerism
  • Thioacetamide / analogs & derivatives*
  • Thioacetamide / chemical synthesis*

Substances

  • Ketones
  • Thioacetamide