Abstract
This paper reveals a novel "boomerang" strategy in the expedient and diastereoselective synthesis of C-nucleoside analogues. Bench-stable ortho-isocyanophenyl thioglycosides can be converted to glycosyl radicals through rapid and efficient C-S bond homolysis when they are irradiated by visible light. The glycosyl radicals are subsequently trapped by the corresponding leaving group or other radical acceptors to provide diverse C-nucleoside analogues under mild conditions.
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