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

Mélissa Boultadakis-Arapinis; Pascale Lemoine; Serge Turcaud; Laurent Micouin; Thomas Lecourt

doi:10.1021/ja1054065

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.

Authors

Mélissa Boultadakis-Arapinis¹, Pascale Lemoine, Serge Turcaud, Laurent Micouin, Thomas Lecourt

Affiliation

¹ Laboratoire de Chimie Thérapeutique (UMR CNRS 8638), Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4, avenue de l'Observatoire, 75006 Paris, France.

PMID: 20961097
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