Iron-catalyzed iodonium ion promoted activation of conventional thioglycosides for stereoselective 1,2-cis furanosylations

Abstract

Iron-catalyzed activation of conventional thioglycosides using the iodonium ion enabled the selective synthesis of 1,2-cis furanosides. This strategy accommodates diverse furanosyl donors (D-ribose, D-arabinose, L-arabinose) and various O-nucleophiles (1°, 2°, 3°). Additionally, 1,2-cis hexaribofuranoside was synthesized, and the influence of the C2 functional group on selectivity was investigated.