Rh(II) carbene-promoted activation of the anomeric C-H bond of carbohydrates: a stereospecific entry toward α- and β-ketopyranosides

J Am Chem Soc. 2010 Nov 10;132(44):15477-9. doi: 10.1021/ja1054065.

Abstract

In this communication we report a new strategy toward ketopyranosides based on a carbene-mediated activation of the anomeric C-H bond of carbohydrates. By forming a new carbon-carbon bond after a glycosylation step, this approach enables the preparation of both α- and β-ketopyranosides from advanced precursors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Carbohydrates / chemistry*
  • Ketones / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Sequence Data
  • Pyrans / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Carbohydrates
  • Ketones
  • Pyrans
  • carbene
  • Rhodium
  • Methane