Formation and reactivity of novel pyranosidic nicholas oxocarbenium ions: access to C-ketosides and branched-chain C-ketosides

Org Lett. 2006 Jul 20;8(15):3187-90. doi: 10.1021/ol060929+.

Abstract

[Structure: see text] Dicobalt hexacarbonyl propargyl complexes, prepared from alkynyl ketoses, display an unexpected reactivity when treated with Lewis acids in the presence of nucleophiles and furnish C-ketosides, branched-chain C-ketosides, or branched-chain C-glycals depending on the nucleophile and the carbohydrate starting material.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemistry
  • Catalysis
  • Cobalt / chemistry*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Stereoisomerism

Substances

  • Carbohydrates
  • Glycosides
  • Organometallic Compounds
  • Cobalt