Rh(II) carbene-promoted activation of the anomeric C-H bond of carbohydrates: a stereospecific entry toward α- and β-ketopyranosides.
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.
Laboratoire de Chimie Thérapeutique (UMR CNRS 8638), Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4, avenue de l'Observatoire, 75006 Paris, France.
Mélissa
M
Boultadakis-Arapinis
Pascale
P
Lemoine
Serge
S
Turcaud
Laurent
L
Micouin
Thomas
T
Lecourt
D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008969:Molecular Sequence Data; D011714:Pyrans / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D002241:Carbohydrates; D007659:Ketones; D011714:Pyrans; C030011:carbene; D012238:Rhodium; D008697:Methane