Glycosyl Radical-Based Synthesis of <i>C</i>-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade
Jian-Yu Pang, Li-Min Feng, Wenfeng Zhang, De-Yong Liu, Jing Wang, Ruohan Wei, Xiang‐Guo Hu
Abstract
We have developed a glycosyl radical-based synthesis of C -alkyl glycosides through a deoxygenative Giese addition–reduction–cyclization cascade, in which readily available 1-hydroxy carbohydrates serve as precursors for glycosyl radicals and aryl alkenes function as radical acceptors. This reaction not only provides an effective method for accessing a previously underexplored class of functionalized cyclopropanes but also enhances the application of Giese addition in the synthesis of C -alkyl glycosides by derivatizing the radical intermediate generated through polar cyclization to yield a cyclopropane.
Topics & Concepts
ChemistryCyclopropaneGlycosylAlkylCascadeGlycosyl donorOlefin fiberRadical cyclizationStereochemistryStereoselectivityOrganic chemistryCatalysisRing (chemistry)ChromatographyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods