Stereoselective Synthesis of 2-Deoxy-α-N-Glycosides from Glycals with 1,4,2-Dioxazol-5-ones  

作　　者：Zhenpeng Shen Guoyin Yin Yangyang Li 

机构地区：[1]The Institute for Advanced Studies,Wuhan University,Wuhan,Hubei 430072,China

出　　处：《Chinese Journal of Chemistry》2024年第18期2147-2152,共6页中国化学（英文版）

基　　金：supported by the National Natural Science Foundation of China(22122107).

摘　　要：The synthesis of N-glycosides has received significant attention due to their crucial role in carbohydrate chemistry.Despite considerable advancements developed in the construction of N-glycosides,methods for the stereoselective construction of 2-deoxy-α-N-glycosides are still limited.Herein,we disclosed a nickel-catalyzed hydroamination of glycals under mild conditions.This transformation could allow for the stereoselective synthesis of an array of 2-deoxy-α-N-glycosides with excellentα-stereoselectivity.Nickel-catalyzed glycosylation reactions,particularly those involving anomeric C(sp")-metal bond formation,have proven to be an effective and stereoselective strategy for producing various N-glycosides.Additionally,with highlight of the application of this reaction,y-sugar amino acidderivatives weresynthesized.

关 键 词：2-Deoxy-α-N-glycosides Nickel catalysis STEREOSELECTIVITY GLYCALS HYDROAMINATION Amides Glycosylation Alkenes ComprehensiveSummary 

分 类 号：O62[理学—有机化学]