Concise Report
Stereoselective Synthesis of 2-Deoxy-α-N-Glycosides from Glycals with 1,4,2-Dioxazol-5-ones
Zhenpeng Shen,
Guoyin Yin,
Yangyang Li,
Zhenpeng Shen
The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorCorresponding Author
Guoyin Yin
The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei, 430072 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Yangyang Li
The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei, 430072 China
E-mail: [email protected]; [email protected]Search for more papers by this authorZhenpeng Shen,
Guoyin Yin,
Yangyang Li,
Zhenpeng Shen
The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorCorresponding Author
Guoyin Yin
The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei, 430072 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Yangyang Li
The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei, 430072 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
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(sp3)-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.
Supporting Information
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