ArticleJournal of the American Chemical Society2012
Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.
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Who cites it
38 citing papers in PubMed, 193 citations in OpenAlex.
- Recognition of a Conserved Minimal Catalaphile Explains Catalyst Generality in Enantioselective Nitroalkene Reductions.ACS catalysis · 2026Article
- Performance-enhancing asymmetric catalysis unlocks tuning without rebuilding.Chem catalysis · 2025Article
- Performance-Enhancing Asymmetric Catalysis Driven by Achiral Counterion Design.Journal of the American Chemical Society · 2025Article
- Computational Identification of Potential Organocatalysts (CIPOC) Reveals a 2-aminoDMAP/Urea Catalyst Superior to Its Thiourea Analogue.Journal of the American Chemical Society · 2025Article
- Thianthrene/TfOH-catalyzed electrophilic halogenations usingChemical science · 2024Article
- Intramolecular chaperone-assisted dual-anchoring activation (ICDA): a suitable preorganization for electrophilic halocyclization.Chemical science · 2024Article
- Chiral bifunctional sulfide-catalyzed enantioselective bromolactonizations of α- and β-substituted 5-hexenoic acids.Beilstein journal of organic chemistry · 2024Article
- A Catalytic Asymmetric Hydrolactonization.Journal of the American Chemical Society · 2023Article
- Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine.Chemical science · 2022Article
- Are bis(pyridine)iodine(I) complexes applicable for asymmetric halogenation?Organic & biomolecular chemistry · 2021Article
- Oxoammonium salts are catalysing efficient and selective halogenation of olefins, alkynes and aromatics.Nature communications · 2021Article
- A dynamic picture of the halolactonization reaction through a combination ofChemical science · 2021Article
- Catalytic enantioselective bromohydroxylation of cinnamyl alcohols.RSC advances · 2021Article
- Ritter-enabled catalytic asymmetric chloroamidation of olefins.Chemical science · 2020Article
- Association of Halogen Bonding and Hydrogen Bonding in Metal Acetate-Catalyzed Asymmetric Halolactonization.iScience · 2019Article
- The inverted ketene synthon: a double umpolung approach to enantioselective βChemical science · 2019Article
- Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by COJournal of the American Chemical Society · 2019Article
- Enantioselective Organocatalytic Amine-Isocyanate Capture-Cyclization: Regioselective Alkene Iodoamination for the Synthesis of Chiral Cyclic Ureas.ACS catalysis · 2018Article
- Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications.The Journal of organic chemistry · 2018Article
- Absolute and relative facial selectivities in organocatalytic asymmetric chlorocyclization reactions.Chemical science · 2018Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Highly enantioselective halolactonizations have been developed that employ a chiral proton catalyst-N-iodosuccinimide (NIS) reagent system in which the Brønsted acid is used at catalyst loadings as low as 1 mol %. An approach that modulates the achiral counterion (equimolar to the neutral chiral ligand-proton complex present at low catalyst loadings) to optimize the enantioselection is documented for the first time in this transformation. In this way, unsaturated carboxylic acids are converted to γ-lactones in high yields (up to 98% ee) using commercially available NIS.
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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.