ArticleThe Journal of organic chemistry2010
Erosion of stereochemical control with increasing nucleophilicity: O-glycosylation at the diffusion limit.
Article in The Journal of organic chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 43 papers.
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Who cites it
43 citing papers in PubMed.
- AnilineScience advances · 2026Article
- Beyond the two-conformer model: boat conformers provide stereoselectivity in SChemical science · 2026Article
- Article
- Defined Glycan Ligands for Detecting Rare l-Sugar-Binding Proteins.Journal of the American Chemical Society · 2025Article
- The Stereoselectivity of Neighboring Group-Directed Glycosylation Is Concentration-Dependent.Journal of the American Chemical Society · 2025Article
- Diastereoselective Substitution Reactions of Acyclic Acetals Controlled by Remote Participation of an Acyloxy Group.Organic letters · 2024Article
- β-Selective 2-Deoxy- and 2,6-Dideoxyglucosylations Catalyzed by Bis-Thioureas.Journal of the American Chemical Society · 2024Article
- Acetal Substitution Reactions: Stereoelectronic Effects, Conformational Analysis, Reactivity vs. Selectivity, and Neighboring-Group Participation.Synlett : accounts and rapid communications in synthetic organic chemistry · 2024Article
- Origins of Selectivity in Glycosylation Reactions with Saccharosamine Donors.Organic letters · 2023Article
- Reactivity of electrophilic cyclopropanes.Pure and applied chemistry. Chimie pure et appliquee · 2023Article
- Involvement of an Oxonium Ion Intermediate in Controlling the Diastereoselectivity of Nucleophilic Substitution Reactions of Septanoses.Organic letters · 2023Article
- Halogen Atom Participation in Guiding the Stereochemical Outcomes of Acetal Substitution Reactions.Angewandte Chemie (International ed. in English) · 2022Article
- Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.Chemical reviews · 2022Review
- Total synthesis ofChemical science · 2022Article
- Diastereoselective Substitution Reactions of Acyclic β-Alkoxy Acetals via Electrostatically Stabilized Oxocarbenium Ion Intermediates.Organic letters · 2022Article
- Diastereoselective Additions of Allylmagnesium Reagents to α-Substituted Ketones When Stereochemical Models Cannot Be Used.The Journal of organic chemistry · 2021Article
- Reactivity-Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides.Angewandte Chemie (International ed. in English) · 2021Article
- Chemical synthesis of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions.Chemical science · 2020Article
- Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.Chemical reviews · 2020Review
- Bromine-Promoted Glycosidation of Conformationally Superarmed Thioglycosides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
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2 authors.
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Abstract
Nucleophilic substitution reactions of 2-deoxyglycosyl donors indicated that the reactivity of the oxygen nucleophile has a significant impact on stereoselectivity. Employing ethanol as the nucleophile resulted in a 1:1 (alpha:beta) ratio of diastereomers under S(N)1-like reaction conditions. Stereoselective formation of the 2-deoxy-alpha-O-glycoside was only observed when weaker nucleophiles, such as trifluoroethanol, were employed. The lack of stereoselectivity observed in reactions of common oxygen nucleophiles can be attributed to reaction rates of the stereochemistry-determining step that approach the diffusion limit. In this scenario, both faces of the prochiral oxocarbenium ion are subject to nucleophilic addition to afford a statistical mixture of diastereomeric products. Control experiments confirmed that all nucleophilic substitution reactions were performed under kinetic control.
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