Synthesis of 2-Deoxy-C-Glycosides via Iridium-Catalyzed sp2 and sp3 C-H Glycosylation with Unfunctionalized Glycals†

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 LiAlH4.

Automated 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 benzoxazole directing group can be cleanly removed by the treatment of KOH or LiAlH4, offering a versatile method for the synthesis of these glycosides.