ArticleChemical science2016
Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles.
Article in Chemical science, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 42 papers.
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Who cites it
42 citing papers in PubMed, 155 citations in OpenAlex.
- Neutral chiral bidentate tellurium-triazoles for enantioselective non-covalent chalcogen-bonding catalysis.Nature communications · 2026Article
- From Oxygen to Tellurium: The Impact of the Chalcogen on Nucleophilicities and Basicities of Isochalcogenourea Catalysts.Angewandte Chemie (International ed. in English) · 2025Article
- Enantioselective isothiourea-catalysed α-fluorination of C1-ammonium enolates generated from arylesters.Journal of fluorine chemistry · 2025Article
- One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening.Molecules (Basel, Switzerland) · 2024Article
- De-epimerizing DyKAT of β-lactones generated by isothiourea-catalysed enantioselective [2 + 2] cycloaddition.Chemical science · 2024Article
- Enantioselective Synthesis in Continuous Flow: Polymer-Supported Isothiourea-Catalyzed Enantioselective Michael Addition-Cyclization with α-Azol-2-ylacetophenones.Organic process research & development · 2024Article
- Understanding divergent substrate stereoselectivity in the isothiourea-catalysed conjugate addition of cyclic α-substituted β-ketoesters to α,β-unsaturated aryl esters.Chemical science · 2023Article
- Supramolecular catalysis with ethers enabled by dual chalcogen bonding activation.Nature communications · 2023Article
- Enantioselective isothiourea-catalysed reversible Michael addition of aryl esters to 2-benzylidene malononitriles.Chemical science · 2023Article
- Isothiourea-Catalyzed Enantioselective Functionalisation of Glycine Schiff Base Aryl Esters via 1,6- and 1,4-Additions.ChemistryEurope · 2023Article
- Probing Regio- and Enantioselectivity in the Formal [2 + 2] Cycloaddition of C(1)-Alkyl Ammonium Enolates with β- and α,β-Substituted Trifluoromethylenones.The Journal of organic chemistry · 2023Article
- Strategies for the Design of PEDOT Analogues Unraveled: the Use of Chalcogen Bonds and σ-Holes.The journal of physical chemistry. A · 2023Article
- A Desilylative Approach to Alkyl Substituted C(1)-Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions.Angewandte Chemie (International ed. in English) · 2022Article
- Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates andOrganic letters · 2022Article
- Cooperative chalcogen bonding interactions in confined sites activate aziridines.Nature communications · 2022Article
- Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2022Article
- Isothiourea-Catalyzed Enantioselective Michael Addition of Malonates to α,β-Unsaturated Aryl Esters.Organic letters · 2022Article
- Recent progress in asymmetric synergistic catalysis - the judicious combination of selected chiral aminocatalysts with achiral metal catalysts.Organic & biomolecular chemistry · 2022Review
- A Se···O bonding catalysis approach to the synthesis of calix[4]pyrroles.Beilstein journal of organic chemistry · 2022Article
- Isothiourea-Catalyzed Enantioselective α-Alkylation of Esters via 1,6-Conjugate Addition toMolecules (Basel, Switzerland) · 2021Article
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
Abstract
Isothiourea-catalyzed annulations between 2-acyl benzazoles and α,β-unsaturated acyl ammonium intermediates are selectively tuned to form either lactam or lactone heterocycles in good yields (up to 95%) and high ee (up to 99%) using benzothiazole or benzoxazole derivatives, respectively. Computation gives insight into the significant role of two 1,5-S···O interactions in controlling the structural preorganization and chemoselectivity observed within the lactam synthesis with benzothiazoles as nucleophiles. When using benzazoles the absence of a second stabilizing non-bonding 1,5-S···O interaction leads to a dominant C-H···O interaction in determining structural preorganization and lactone formation.
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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.