Fe-catalyzed direct dithioacetalization of aldehydes with 2-chloro-1,3-dithiane

Org Lett. 2014 Sep 5;16(17):4396-9. doi: 10.1021/ol502276r. Epub 2014 Aug 18.

Abstract

Present methods to synthesize 1,3-dithiane molecules require either harsh reaction conditions or highly specialized reagents. We have developed a catalytic dithioacetalization process that directly gains access to the corresponding 1,3-dithianes using aldehydes and 2-chloro-1,3-dithiane in a highly efficient manner. This methodology is beneficial due to mildness of the reaction conditions, and the dithioacetaliation process results in good to excellent yields by using 15 mol % of an iron catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Chlorides / chemistry*
  • Ferric Compounds / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds, 1-Ring / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Quinolizines
  • Stereoisomerism
  • Sulfur Compounds

Substances

  • 2-chloro-1,3-dithiane
  • Aldehydes
  • Chlorides
  • Ferric Compounds
  • Heterocyclic Compounds
  • Heterocyclic Compounds, 1-Ring
  • Indicators and Reagents
  • Quinolizines
  • Sulfur Compounds
  • dithiane
  • 1,3-dithiane
  • ferric chloride