Palladium(II) Acetate Catalyzed Stereoselective C-Glycosidation of Peracetylated Glycals with Arylboronic Acids

Addition of a variety of arylboronic acids to peracetylated glycals takes place in the presence of a catalytic amount of Pd(OAc)2. The reaction involves the syn addition of a σ-aryl-Pd complex to the glycal double bond followed by anti elimination of Pd(OAc)2 to provide a carbon-Ferrier type product. This method provides a practical and convenient stereoselective synthesis of C-arylglycosides.