Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese
Jian-Yu Pang1, Li-Min Feng1, Wen-Feng Zhang1
1National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China.
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.
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