ArticleJournal of the American Chemical Society2016
Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Site Reversal in Nucleophilic Addition to 1,2,3-Triazine 1-Oxides.Journal of the American Chemical Society · 2023Article
- Acyclic and Heterocyclic Azadiene Diels-Alder Reactions Promoted by Perfluoroalcohol Solvent Hydrogen Bonding: Comprehensive Examination of Scope.The Journal of organic chemistry · 2022Article
- Reaction Scope of Methyl 1,2,3-Triazine-5-carboxylate with Amidines and the Impact of C4/C6 Substitution.The Journal of organic chemistry · 2021Article
- Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding.Journal of the American Chemical Society · 2020Article
- Silylium ion mediated 2+2 cycloaddition leads to 4+2 Diels-Alder reaction products.Communications chemistry · 2020Article
- Synthesis, Characterization, and Cycloaddition Reactivity of a Monocyclic Aromatic 1,2,3,5-Tetrazine.Journal of the American Chemical Society · 2019Article
- Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.The Journal of organic chemistry · 2019Review
- Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine.Organic letters · 2018Article
- Computational Exploration of Concerted and Zwitterionic Mechanisms of Diels-Alder Reactions between 1,2,3-Triazines and Enamines and Acceleration by Hydrogen-Bonding Solvents.Journal of the American Chemical Society · 2017Article
- Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.Organic letters · 2017Article
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2 authors.
Funding
Abstract
Although it has been examined for decades, no general approach to catalysis of the inverse electron demand Diels-Alder reactions of heterocyclic azadienes has been introduced. Typically, additives such as Lewis acids lead to nonproductive consumption of the electron-rich dienophiles without productive activation of the electron-deficient heterocyclic azadienes. Herein, we report the first general method for catalysis of such cycloaddition reactions by using solvent hydrogen bonding of non-nucleophilic perfluoroalcohols, including hexafluoroisopropanol (HFIP) and trifluoroethanol (TFE), to activate the electron-deficient heterocyclic azadienes. Its use in promoting the cycloaddition of 1,2,3-triazine 4 with enamine 3 as the key step of a concise total synthesis of methoxatin is described.
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