ArticleOrganic letters2014
Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds.Beilstein journal of organic chemistry · 2023Article
- Enantioselective, Decarboxylative (3+2)-Cycloaddition of Azomethine Ylides and Chromone-3-Carboxylic Acids.Molecules (Basel, Switzerland) · 2022Article
- Three-Component [3+2] Cycloaddition for Regio- and Diastereoselective Synthesis of Spirooxindole-Pyrrolidines.New journal of chemistry = Nouveau journal de chimie · 2022Article
- Pseudo-Five-Component Reaction for Diastereoselective Synthesis of Butterfly Shaped Bispiro[Oxindole-Pyrrolidine]s.The Journal of organic chemistry · 2021Article
- Article
- Construction of hybrid polycyclic quinolinobenzo[a]phenazinone architectures using solid-state melt reaction (SSMR).Molecular diversity · 2021Article
- C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods.SynOpen (2017) · 2021Article
- Acid Catalyzed Formation of C⁻C and C⁻S Bonds via Excited State Proton Transfer.Molecules (Basel, Switzerland) · 2019Article
- Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.Organic letters · 2018Article
- Synthesis of Polycyclic Imidazolidinones via Amine Redox-Annulation.Organic letters · 2017Article
- Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- New Regio- and Stereoselective Cascades via Unstabilized Azomethine Ylide Cycloadditions for the Synthesis of Highly Substituted Tropane and Indolizidine Frameworks.Journal of the American Chemical Society · 2016Article
- C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.Chemical communications (Cambridge, England) · 2015Article
- The Rügheimer-Burrows reaction revisited: Facile preparation of 4-alkylisoquinolines and 3,5-dialkylpyridines from (partially) saturated amines.Tetrahedron letters · 2015Article
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3 authors.
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Abstract
Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetrahydroisoquinolines or tryptolines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereoselective fashion to form polycyclic amines with four new stereogenic centers. Challenging substrates such as piperidine, morpholine, and thiomorpholine undergo the corresponding reactions at elevated temperatures.
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