Synthesis of <scp>2‐Deoxy‐<i>C</i>‐Glycosides</scp> via <scp>Iridium‐Catalyzed</scp> sp<sup>2</sup> and sp<sup>3</sup> C—H Glycosylation with Unfunctionalized Glycals<sup>†</sup>
Wanjun Zhu, Qikai Sun, Hai Won Chang, Huixing Zhang, Quanquan Wang, Gong Chen, Gang He
Abstract
Comprehensive Summary A new protocol for the synthesis of 2‐deoxy‐ C ‐aryl‐glycosides and 2‐deoxy‐ C ‐alkyl‐glycosides via iridium‐catalyzed directed C—H glycosylation with glycals is reported. The method is amenable for both the C 2 C—H glycosylation of indoles and the methyl C—H glycosylation of secondary methyl amines under the control of an N ‐linked benzoxazole directing group. The benzoxazole group can be cleanly removed by the treatment of KOH or LiAlH 4 .
Topics & Concepts
ChemistryGlycosylationBenzoxazoleCatalysisStereochemistryGlycosideArylN-linked glycosylationIridiumAlkylOrganic chemistryBiochemistryGlycanGlycoproteinCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSynthesis and Biological Evaluation