ArticleJournal of the American Chemical Society2017
Glycosyl Cross-Coupling of Anomeric Nucleophiles: Scope, Mechanism, and Applications in the Synthesis of Aryl C-Glycosides.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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31 citing papers in PubMed, 138 citations in OpenAlex.
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- Diverse Synthesis of C-Glycosides by Stereoselective Ni-Catalyzed Carboboration of Glycals.Journal of the American Chemical Society · 2024Article
- Pd-Catalyzed Arylation of Secondary α-Alkoxytricyclohexylstannanes.Organic letters · 2022Article
- Recent Advances on Natural Aryl-Molecules (Basel, Switzerland) · 2022Review
- Remote C-H Glycosylation by Ruthenium(II) Catalysis: Modular Assembly of meta-C-Aryl Glycosides.Angewandte Chemie (International ed. in English) · 2022Article
- P(v) intermediate-mediated E1cB elimination for the synthesis of glycals.Chemical science · 2022Article
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- Advances in Pd-catalyzed C-C bond formation in carbohydrates and their applications in the synthesis of natural products and medicinally relevant molecules.RSC advances · 2021Review
- Organometallic AlaChem catalysis · 2021Article
- Nickel-Catalyzed Radical Migratory Coupling Enables C-2 Arylation of Carbohydrates.Journal of the American Chemical Society · 2021Article
- Light-Mediated Cross-Coupling of Anomeric Trifluoroborates.Organic letters · 2021Article
- Diastereoselective Synthesis of Aryl C-Glycosides from Glycosyl Esters via C-O Bond Homolysis.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
Abstract
Stereoselective manipulations at the C1 anomeric position of saccharides are one of the central goals of preparative carbohydrate chemistry. Historically, the majority of reactions forming a bond with anomeric carbon has focused on reactions of nucleophiles with saccharide donors equipped with a leaving group. Here, we describe a novel approach to stereoselective synthesis of C-aryl glycosides capitalizing on the highly stereospecific reaction of anomeric nucleophiles. First, methods for the preparation of anomeric stannanes have been developed and optimized to afford both anomers of common saccharides in high anomeric selectivities. We established that oligosaccharide stannanes could be prepared from monosaccharide stannanes via O-glycosylation with Schmidt-type donors, glycal epoxides, or under dehydrative conditions with C1 alcohols. Second, we identified a general set of catalytic conditions with Pd
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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.