Functionalization of GlucoPyranosides at position 5 by 1,5 C–H insertion of Rh(II)-Carbenes: Dramatic influence of the anomeric configuration

Jana Hammoud (1) , Antoine Joosten (1) , Thomas Lecourt (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Herein, a C–H bond functionalization approach is reported as a new route towards non-natural glycosides having a quaternary position 5. The development of this transformation furthermore reveals that insertion of Rh(II)-carbenes into the C5–H bond is controlled by remote stereoelectronic effects induced by the axial or equatorial orientation of the aglycone.

Mots clés: C-H bond functionalization; Rh(II)-carbene; Quaternarization; Stereoelectronic effects

Domaines: Chimie

Jana Hammoud, Antoine Joosten, Thomas Lecourt. Functionalization of GlucoPyranosides at position 5 by 1,5 C–H insertion of Rh(II)-Carbenes: Dramatic influence of the anomeric configuration. Carbohydrate Research, 2019, 486, pp.107834. ⟨10.1016/j.carres.2019.107834⟩. ⟨hal-02548495⟩