ArticleOrganic letters2011
Phosphine-initiated general base catalysis: facile access to benzannulated 1,3-diheteroatom five-membered rings via double-Michael reactions of allenes.
Article in Organic letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Enantioselective phosphine-catalyzed [6 + 1] annulations of α-allyl allenoates with 1,1-bisnucleophiles.Chemical science · 2024Article
- Synthesis of 3,4-Disubstituted Maleimide Derivatives via Phosphine-Catalyzed Isomerization of α-Succinimide-Substituted Allenoates Cascade γ'-Addition with Aryl Imines.International journal of molecular sciences · 2024Article
- Phosphine-Catalyzed γ'-Carbon 1,6-Conjugate Addition of α-Succinimide Substituted Allenoates withMolecules (Basel, Switzerland) · 2024Article
- Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates.ChemCatChem · 2020Article
- Organophosphine-Catalyzed [4C+X] Annulations.Molecules (Basel, Switzerland) · 2018Review
- Phosphine Organocatalysis.Chemical reviews · 2018Review
- Syntheses of Highly Functionalized Spirocyclohexenes by Formal [4+2] Annulation of Arylidene Azlactones with Allenoates.Asian journal of organic chemistry · 2018Article
- Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones withChemical science · 2018Article
- Formal (4 + 1)-Addition of Allenoates to o-Quinone Methides.Organic letters · 2018Article
- Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes.Organic letters · 2016Article
- (4+1) vs (4+2): Catalytic Intramolecular Coupling between Cyclobutanones and Trisubstituted Allenes via C-C Activation.Journal of the American Chemical Society · 2015Article
- Stereoselective Syntheses of α,β-Unsaturated γ-Amino Esters Through Phosphine-Catalyzed γ-Umpolung Additions of Sulfonamides to γ-Substituted Allenoates.Tetrahedron letters · 2015Article
- Synthesis of tetrasubstituted 1-silyloxy-3-aminobutadienes and chemistry beyond Diels-Alder reactions.Nature communications · 2015Article
- Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins.Beilstein journal of organic chemistry · 2014Article
- Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.Chemical communications (Cambridge, England) · 2013Article
- Bimolecular Coupling Reactions through Oxidatively Generated Aromatic Cations: Scope and Stereocontrol.Tetrahedron · 2013Article
- Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines.Chemical communications (Cambridge, England) · 2012Article
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Abstract
General base-catalyzed double-Michael reactions of allenes with various dinucleophiles are described. The reactions are facilitated most efficiently by a catalytic amount of trimethylphosphine, affording six types of C2-functionalized benzannulated five-membered heterocycles: benzimidazolines, benzoxazolines, benzothiazolines, 1,3-benzodioxoles, 1,3-benzoxathioles, and 1,3-benzodithioles. This atom-economical reaction is operationally simple and provides the product heterocycles in good to excellent yields. Careful mechanistic studies unveiled the phosphine-triggered general base catalysis pathway. Furthermore, the double-Michael reaction can serve as an alternative method for the selective monoketalization of β-diketones.
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