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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
Wuhan University
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Guoyin Yin
Wuhan University
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Yangyang Li
Wuhan University

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The synthesis of N-glycosides has received significant attention due to their crucial role in carbohydrate chemistry. Despite considerable advancements were 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 effec-tive and stereoselective strategy for producing various N-glycosides. Additionally, with highlight the application of this reaction, γ-sugar amino acid derivatives were synthesized by one step.
23 Feb 2024Submitted to Chinese Journal of Chemistry
04 Mar 2024Reviewer(s) Assigned
18 Mar 2024Review(s) Completed, Editorial Evaluation Pending
22 Mar 2024Editorial Decision: Revise Minor