ArticleJournal of the American Chemical Society2024
Diverse Synthesis of C-Glycosides by Stereoselective Ni-Catalyzed Carboboration of Glycals.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Stereocontrolled entry to borylated piperidinesChemical science · 2026Article
- Site-Selective Distal Arylation of Sugars Enabled by Cyclic Acetals.Journal of the American Chemical Society · 2026Article
- Ligand-enabled next-generation glycosyl Stille cross-coupling for the stereospecific synthesis of sterically hindered aryl C-glycosides.Nature communications · 2026Article
- Synthesis of Diverse Glycosyl Bicyclo[1.1.1]pentanes Enabled by Electrochemical Functionalization of [1.1.1]Propellane.Journal of the American Chemical Society · 2025Article
- Synthesis of Borylated Orphaned Cyclopropanes through a Boron-Enabled Cycloisomerization Reaction.Journal of the American Chemical Society · 2025Article
- Carbohydrate Synthesis is Entering the Data-Driven Digital Era.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Creating glycoside diversity through stereoselective carboboration of glycals.Nature communications · 2024Article
- ZnIMolecules (Basel, Switzerland) · 2024Review
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Authors and funding
3 authors.
Funding
Abstract
C-Glycosides are important structures that are common to natural products and pharmaceutical agents. Established methods for their synthesis involve the reaction of an activated anomeric carbon. In this study, we report a conceptually new approach that involves the stereoselective Ni-catalyzed carboboration of glycals. In these reactions, not only is a C-C bond formed at the anomeric carbon, but a synthetically useful C-B bond is also installed. Upon C-B oxidation, differentially protected C-glycosides to be formed. In addition, stereospecific manipulation of the C-B bond leads to diverse C-glycosides. Finally, we report the application of this method in the synthesis of established C-glycosides, such as C-glycosyl amino acids, as well as a strategy to make all possible diastereomers at C1 and C2.
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