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

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

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The synthesis of N-glycosides has received significant attention due to their crucial role in carbohydrate chemistry.Despite considera-ble advancements developed in the construction of N-glycosides,methods for the stereoselective construction of 2-deoxy-a-N-glyco-sides αre 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 excellent α-stereoselectivity.Nickel-catalyzed glycosylation reactions,particularly those involving anomeric C(sp3)-metal bond formation,have proven to be an effective and stere-oselective strategy for producing various N-glycosides.Additionally,with highlight of the application of this reaction,y-sugar amino acid derivatives were synthesized.

2-Deoxy-α-N-glycosidesNickel catalysisStereoselectivityGlycalsHydroaminationAmidesGlycosylationAlkenes

Zhenpeng Shen、Guoyin Yin、Yangyang Li

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The Institute for Advanced Studies,Wuhan University,Wuhan,Hubei 430072,China

2024

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子:0.848
ISSN:1001-604X
年,卷(期):2024.42(18)