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

Zhenpeng Shen; Guoyin Yin; Yangyang Li

doi:10.1002/cjoc.202400224

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (18) : 2147 -2152. DOI: 10.1002/cjoc.202400224

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

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Abstract

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 excellent α-stereoselectivity. Nickel-catalyzed glycosylation reactions, particularly those involving anomeric C(sp ³)-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, γ-sugar amino acid derivatives were synthesized.

Keywords

2-Deoxy- α-N-glycosides / Nickel catalysis / Stereoselectivity / Glycals / Hydroamination / Amides / Glycosylation / Alkenes

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Zhenpeng Shen, Guoyin Yin, Yangyang Li. Stereoselective Synthesis of 2-Deoxy-α-N-Glycosides from Glycals with 1, 4, 2-Dioxazol-5-ones. Chinese Journal of Chemistry, 2024, 42(18): 2147-2152 DOI:10.1002/cjoc.202400224