ArticleJournal of the American Chemical Society2018
Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 64 citations in OpenAlex.
- Diastereoselective Synthesis ofACS catalysis · 2026Article
- Enantioselective Pictet-Spengler-Type Reaction via a Helically Chiral Anion as an Access to 4,5-Dihydropyrrolo[1,2-The Journal of organic chemistry · 2025Article
- Chloride-Mediated Alkene Activation Drives Enantioselective Thiourea and Hydrogen Chloride Co-Catalyzed Prins Cyclizations.Journal of the American Chemical Society · 2022Article
- Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.Journal of the American Chemical Society · 2021Article
- Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides.Organic letters · 2021Article
- Highly Selective Ortho-Directed Dicarboxylation of Cyclopentadiene by Methylcarbonates and COChemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Hydrogen Bond Donor Catalyzed Cationic Polymerization of Vinyl Ethers.Angewandte Chemie (International ed. in English) · 2021Article
- Enantioselective PCCP Brønsted acid-catalyzed aminalization of aldehydes.Beilstein journal of organic chemistry · 2021Article
- Cooperative Catalysis for the Highly Diastereo- and Enantioselective [4+3]-Cycloannulation of ortho-Quinone Methides and Carbonyl Ylides.Angewandte Chemie (International ed. in English) · 2020Article
- Controlled Cationic Polymerization: Single-Component Initiation under Ambient Conditions.Journal of the American Chemical Society · 2019Article
- Synthesis of α-heterosubstituted ketones through sulfur mediated difunctionalization of internal alkynes.Chemical science · 2019Article
- Article
- Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes - a reaction at the 'oxonium-Prins'Chemical science · 2019Article
- A Cooperative Hydrogen Bond Donor-Brønsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans.Angewandte Chemie (International ed. in English) · 2018Article
- Silylated cyclopentadienes as competent silicon Lewis acid catalysts.Chemical science · 2018Article
- Chiral Pentacarboxycyclopentadiene-Based Brønsted Acid-Catalyzed Enantioselective Desymmetrization of Meso-Epoxides by 2-Mercaptobenzothiazoles.ACS omega · 2018Article
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 1 country.
Funding
Abstract
An enantioselective catalytic inverse-electron-demand Diels-Alder reaction of salicylaldehyde acetal-derived oxocarbenium ions and vinyl ethers to generate 2,4-dioxychromanes is described. Chiral pentacarboxycyclopentadiene (PCCP) acids are found to be effective for a variety of substrates. Computational and X-ray crystallographic analyses support the unique hypothesis that an anion with point-chirality-induced helical chirality dictates the absolute sense of stereochemistry in this reaction.
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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.