Glycosyl Radical-Based\nSynthesis of <i>C</i>‑Alkyl Glycosides Bearing a\nCyclopropane via a Deoxygenative\nGiese Addition–Reduction–Cyclization Cascade

We have developed a glycosyl radical-based\nsynthesis\nof <i>C</i>-alkyl glycosides through a deoxygenative Giese\naddition–reduction–cyclization\ncascade, in which readily available 1-hydroxy carbohydrates serve\nas precursors for glycosyl radicals and aryl alkenes function as radical\nacceptors. This reaction not only provides an effective method for\naccessing a previously underexplored class of functionalized cyclopropanes\nbut also enhances the application of Giese addition in the synthesis\nof <i>C</i>-alkyl glycosides by derivatizing the radical\nintermediate generated through polar cyclization to yield a cyclopropane.