ArticleNature chemistry2023
A synergistic Rh(I)/organoboron-catalysed site-selective carbohydrate functionalization that involves multiple stereocontrol.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Fucoidans: a new frontier in brown seaweed research and biotechnology.Cell surface (Amsterdam, Netherlands) · 2026Review
- Carbene-catalyzed site-selective sulfonylation and modular edition of monosaccharides for hydroxyl group stereoinversion and swapping.Nature communications · 2026Article
- Sequential Regiodivergent Polyol Sulfonylation and Functionalization Enable Precise Engineering of Carbohydrates.JACS Au · 2026Article
- Catalytic Strategies for Stereoselective Carbohydrate Synthesis: Emerging Concepts for Accessing Challenging Glycosides.Angewandte Chemie (International ed. in English) · 2025Review
- Electrochemical Ammoxidation of Unprotected Glycosides.ACS electrochemistry · 2025Article
- Emerging Capabilities of Nonclassical Noncovalent Interactions and Asymmetric Catalysis in Stereoselective Glycosylations and Carbohydrate Functionalizations.Accounts of chemical research · 2025Article
- Rh(II) and Chiral Phosphoric Acid Co-catalyzed Selective O-H Insertions for StereodivergentJournal of the American Chemical Society · 2025Article
- Carbene-catalyzed chirality-controlled site-selective acylation of saccharides.Nature communications · 2025Article
- Article
- Harnessing Multistep Chalcogen Bonding Activation in the α-Stereoselective Synthesis of Iminoglycosides.Journal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Site-selective functionalization is a core synthetic strategy that has broad implications in organic synthesis. Particularly, exploiting chiral catalysis to control site selectivity in complex carbohydrate functionalizations has emerged as a leading method to unravel unprecedented routes into biologically relevant glycosides. However, robust catalytic systems available to overcome multiple facets of stereoselectivity challenges to this end still remain scarce. Here we report a synergistic chiral Rh(I)- and organoboron-catalysed protocol, which enables access into synthetically challenging but biologically relevant arylnaphthalene glycosides. Our method depicts the employment of chiral Rh(I) catalysis in site-selective carbohydrate functionalization and showcases the utility of boronic acid as a compatible co-catalyst. Crucial to the success of our method is the judicious choice of a suitable organoboron catalyst. We also determine that exquisite multiple aspects of stereocontrol, including enantio-, diastereo-, regio- and anomeric control and dynamic kinetic resolution, are concomitantly operative.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.