ArticleNature communications2018
An ultra-low thiourea catalyzed strain-release glycosylation and a multicatalytic diversification strategy.
Article in Nature communications, 2018. 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.
- Charting the Future of Stereoselective Carbohydrate Synthesis: The Essential Role of Cross-Disciplinary Innovation.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Enhanced Selectivity of Chalcogen Bonding over Halogen Bonding Catalyzed C-glycosylation Through Differentiated Intermediate Activation.Angewandte Chemie (International ed. in English) · 2026Article
- Hexafluoroisopropanol-Promoted Stereospecific Glycosylation Enables Efficient Access to N-O-Linked 1,2-JACS Au · 2025Article
- Emerging Capabilities of Nonclassical Noncovalent Interactions and Asymmetric Catalysis in Stereoselective Glycosylations and Carbohydrate Functionalizations.Accounts of chemical research · 2025Article
- Stereoselective Conversions of Carbohydrate Anomeric Hydroxyl Group in Basic and Neutral Conditions.Molecules (Basel, Switzerland) · 2024Review
- EfficientChemical science · 2024Article
- Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Use of Novel Homochiral Thioureas Camphor Derived as Asymmetric Organocatalysts in the Stereoselective Formation of Glycosidic Bonds.Molecules (Basel, Switzerland) · 2024Article
- Cooperative Bifurcated Chalcogen Bonding and Hydrogen Bonding as Stereocontrolling Elements for Selective Strain-Release Septanosylation.Journal of the American Chemical Society · 2023Article
- Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors.Nature communications · 2023Article
- A synergistic Rh(I)/organoboron-catalysed site-selective carbohydrate functionalization that involves multiple stereocontrol.Nature chemistry · 2023Article
- Hydrogen bond activated glycosylation under mild conditions.Chemical science · 2022Article
- Recent advances in stereoselective 1,2-Frontiers in chemistry · 2022Review
- Exploiting non-covalent interactions in selective carbohydrate synthesis.Nature reviews. Chemistry · 2021Review
- A robust and tunable halogen bond organocatalyzed 2-deoxyglycosylation involving quantum tunneling.Nature communications · 2020Article
- Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.Journal of the American Chemical Society · 2020Article
- Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors.Journal of the American Chemical Society · 2020Article
- Recent Developments in Stereoselective Chemical Glycosylation.Asian journal of organic chemistry · 2019Article
Corrections and comments
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Authors and funding
2 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The utility of thiourea catalysis in selective glycosylation strategies has gained significant momentum lately due to its versatility in hydrogen bonding or anionic recognition activation modes. The use of these non-covalent interactions constitute a powerful means to construct glycosidic linkages as it mimics physiologically occurring glycosyltransferases. However, glycosyl donor activation through the currently employed catalysts is moderate such that, in general, catalyst loadings are rather high in these transformations. In addition, thiourea catalysis has not been well explored for the synthesis of furanosides. Herein, we demonstrate an ultra-low loadings stereoselective and stereospecific thiourea catalyzed strain-release furanosylation and pyranosylation strategy. Our ultra-low organocatalyzed furanosylation enables a multicatalytic strategy, which opens up a unique avenue towards rapid diversification of synthetic glycosides. In-situ NMR monitoring unravel insights into unknown reaction intermediates and initial rate kinetic studies reveal a plausible synergistic hydrogen bonding/Brønsted acid activation mode.
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