Access to C-aryl/alkenylglycosides by directed Pd-catalyzed C-H functionalisation of the anomeric position in glycal-type substrates.
Morgane de RobichonAndrea BordessaMaciej MalinowskiJacques UzielNadège Lubin-GermainAngélique FerryPublished in: Chemical communications (Cambridge, England) (2019)
Directed palladium-catalyzed C-H functionalisation of C2-amido glycals onto the anomeric position is described as a novel route to C-aryl/alkenylglycosides. An aminoquinoline-type directing group was used to successfully introduce diverse (hetero)aryl and alkenyl groups at position 1 of the sugar (20 examples). Its application to the synthesis of a dapagliflozin analogue is presented.
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