ArticleThe Journal of organic chemistry2016
Discovery and Development of a Three-Component Oxidopyrylium [5 + 2] Cycloaddition.
Article in The Journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 30 citations in OpenAlex.
- Cycloadditions as a Sweet Route to 'DoubleBiomolecules · 2025Article
- Carbocycloaddition Strategies for Troponoid Synthesis.Tetrahedron · 2023Article
- Synthesis of Polyoxygenated Tropolones and their Antiviral Activity against Hepatitis B Virus and Herpes Simplex Virus-1.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Investigations into a Stoichiometrically Equivalent Intermolecular Oxidopyrylium [5 + 2] Cycloaddition Reaction Leveraging 3-Hydroxy-4-pyrone-Based Oxidopyrylium Dimers.The Journal of organic chemistry · 2021Article
- Synthesis of aryl-substituted 2-methoxyphenol derivatives from maltol-derived oxidopyrylium cycloadducts through an acid-mediated ring contraction cascade.Chemical communications (Cambridge, England) · 2020Article
- Maltol- and Allomaltol-Derived Oxidopyrylium Ylides: Methyl Substitution Pattern Kinetically Influences [5 + 3] Dimerization versus [5 + 2] Cycloaddition Reactions.The Journal of organic chemistry · 2019Article
- Amidation Strategy for Final-Step α-Hydroxytropolone Diversification.Tetrahedron letters · 2018Article
- Oxidopyrylium [5+2] Cycloaddition Chemistry: Historical Perspective and Recent Advances (2008-2018).Tetrahedron · 2018Article
- Fluorous-Phase Approach to α-Hydroxytropolone Synthesis.The Journal of organic chemistry · 2018Article
- Synthesis and biological assessment of 3,7-dihydroxytropolones.Organic & biomolecular chemistry · 2017Article
- Catalytic Enantioselective Intermolecular [5 + 2] Dipolar Cycloadditions of a 3-Hydroxy-4-pyrone-Derived Oxidopyrylium Ylide.Organic letters · 2017Article
- Traceless Solid-Phase α-Hydroxytropolone Synthesis.MedChemComm · 2016Article
Corrections and comments
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Authors and funding
4 authors at 3 institutions in 1 country.
Funding
Abstract
α-Hydroxy-γ-pyrone-based oxidopyrylium cycloaddition reactions are useful methods for accessing a highly diverse range of oxabicyclo[3.2.1]octane products. Intermolecular variants of the reaction require the formation of a methyl triflate-based pre-ylide salt that upon treatment with base in the presence of alkenes or alkynes leads to α-methoxyenone-containing bicyclic products. Herein, we describe our discovery that the use of ethanol-stabilized chloroform as solvent leads to the generation of α-ethoxyenone-containing bicyclic byproducts. This three-component process was further optimized by gently heating a mixture of a purified version of the oxidopyrylium dimer in the presence of an alcohol prior to addition of a dipolarophile. Using this convenient procedure, several new oxidopyrylium cycloaddition products can be generated in moderate yields. We also highlight the method in a tandem ring-opening/debenzylation method for the generation of α-hydroxytropolones.
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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.