Directed Palladium‐Catalyzed <i>pseudo</i>‐Anomeric C−H Functionalization of Glycal‐Type Substrates: Access to Unsymmetrical <i>gem</i>‐Diarylmethyl <i>C</i>‐Glycosides
Atul Dubey, Neha Singh Chauhan, Zanjila Azeem, Pintu Kumar Mandal
Abstract
Pd(II)-Catalyzed, bidentate directing group (BDG)-assisted C(sp2)−H functionalization of C2-amido glycals onto the anomeric position is described as a contemporary method for the construction of various unsymmetrical gem-diarylmethyl C-glycosides. Thanks to a bidentate amidoquinoline-type directing group, the insertion of diverse para-quinone methides (p-QMs) onto the pseudo-anomeric position of glycal substrates were executed in moderate to good yields. Further functionalization of the final product can be successfully demonstrated by known palladium-catalyzed cross-coupling reactions.
Topics & Concepts
ChemistryAnomerGlycalPalladiumSurface modificationDenticityCatalysisStereochemistryCombinatorial chemistryOrganic chemistryStereoselectivityCrystal structurePhysical chemistryCatalytic C–H Functionalization MethodsSynthesis of Indole DerivativesSynthesis and Catalytic Reactions