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

Abstract

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.