Access to C-aryl/alkenylglycosides by directed Pd-catalyzed C-H functionalisation of the anomeric position in glycal-type substrates

Directed palladium-catalyzed C-H functionalisation of C2-amido glycals onto the anomeric position is described as novel access to C-aryl/alkenylglycosides. Aminoquinoline-type directing group was used to successfully introduce diverse (hetero)aryl and alkenyl groups at the position 1 of the sugar (20 examples). Application to the synthesis of a Dapagliflozin analogue is presented.