Diastereoselective metal-catalyzed synthesis of C-aryl and C-vinyl glycosides

Angew Chem Int Ed Engl. 2012 Oct 29;51(44):11101-4. doi: 10.1002/anie.201204786. Epub 2012 Sep 28.

Abstract

Cobalt, the catalyst of choice: The diastereoselective cobalt-catalyzed cross-coupling of 1-bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac)(3)]/tmeda (acac = acetylacetonate, tmeda = N,N'-tetramethylethylenediamine), gives full α selectivity in the mannose and galactose series, and an α selectivity in the glucose series with α/β ratios of 1.3:1-3:1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

  • Glycosides
  • Organometallic Compounds
  • Cobalt
  • Iron