Thiourea-Catalyzed Glycosylation of C,N -Diaryl Glycosyl Imidates

Abstract We report a hydrogen bond-mediated glycosylation protocol employing a new class of C,N-diaryl imidate glycosyl donors bearing two para-fluorophenyl groups, enabling highly efficient and stereoselective glycosylation across a broad range of acceptors. A mechanistic study revealed that thiourea catalysts activate the C,N-diaryl imidate glycosyl donors by forming a noncovalent donor-catalyst complex through hydrogen-bonds. Furthermore, the mild activation conditions and distinct reactivity of C,N-diaryl imidate glycosyl donors facilitate their application in various one-pot oligosaccharide synthesis strategies.