ArticleJournal of the American Chemical Society2020
Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Development, Scope, and Catalyst Selection in Boron-Catalyzed Iterative Glycosylation.Journal of the American Chemical Society · 2025Article
- Catalytic photoinduced deoxygenation via B(CNature communications · 2025Article
- Synthesis of 2-Amino-2-deoxy Sugars via Boron-Catalyzed Coupling of Glycosyl Fluorides and Silyl Ether Acceptors.Organic letters · 2024Article
- Development of Recyclable Polystyrene-Supported Phosphonic Acid Resins for Carbohydrate Immobilization and Glycosylation.The Journal of organic chemistry · 2023Article
- Deoxyfluorination of 1°, 2°, and 3° Alcohols by Nonbasic O-H Activation and Lewis Acid-Catalyzed Fluoride Shuttling.Journal of the American Chemical Society · 2023Article
- Recent Progress in 1,2-Molecules (Basel, Switzerland) · 2023Review
- Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors.Nature communications · 2023Article
- Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.Chemical reviews · 2022Review
- Vessel effects in organic chemical reactions; a century-old, overlooked phenomenon.Chemical science · 2022Review
- Glycosyl Exchange of Unactivated Glycosidic Bonds: Suppressing or Embracing Side Reactivity in Catalytic Glycosylations.The Journal of organic chemistry · 2022Article
- Recent advances in stereoselective 1,2-Frontiers in chemistry · 2022Review
- Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Organic letters · 2021Article
- A Mechanistic Probe into 1,2-Advanced synthesis & catalysis · 2021Article
- Stereoselective β-mannosylations and β-rhamnosylations from glycosyl hemiacetals mediated by lithium iodide.Chemical science · 2021Article
- Protecting-group-freeGreen chemistry : an international journal and green chemistry resource : GC · 2021Article
- Narratives of Undergraduate Research, Mentorship, and Teaching at UCLA.Pure and applied chemistry. Chimie pure et appliquee · 2021Article
- Metal-free glycosylation with glycosyl fluorides in liquid SOBeilstein journal of organic chemistry · 2021Article
- Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride.Organic letters · 2021Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Challenges in the assembly of glycosidic bonds in oligosaccharides and glycoconjugates pose a bottleneck in enabling the remarkable promise of advances in the glycosciences. Here, we report a strategy that applies unique features of highly electrophilic boron catalysts, such as tris(pentafluorophenyl)borane, in addressing a number of the current limitations of methods in glycoside synthesis. This approach utilizes glycosyl fluoride donors and silyl ether acceptors while tolerating the Lewis basic environment found in carbohydrates. The method can be carried out at room temperature using air- and moisture-stable forms of the catalyst, with loadings as low as 0.5 mol %. These characteristics enable a wide array of glycosylation patterns to be accessed, including all C1-C2 stereochemical relationships in the glucose, mannose, and rhamnose series. This method allows one-pot, iterative glycosylations to generate oligosaccharides directly from monosaccharide building blocks. These advances enable the rapid and experimentally straightforward preparation of complex oligosaccharide units from simple building blocks.
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