ArticleRSC advances2021
[3+2] regioselective annulation reaction of 2-arylidene-1,3-indandiones towards synthesis of spirocyclopentenes: understanding the mechanism of γ-attack
Article in RSC advances, 2021. 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, 17 citations in OpenAlex.
- Organocatalytic Formal (3+2+1)-Cycloaddition of Allenoates, Michael Acceptors, and Carbaldehydes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Catalyst-Controlled Divergent Annulation Reactions of Allenoates and Fully Substituted 1,3-Indandione Derived Electron-Deficient Alkenes.The Journal of organic chemistry · 2026Article
- Triple Asymmetric Transfer Hydrogenation of 2-Arylidene-1,3-Indandiones.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Origin of Substituent-Modulated Regioselectivity in Phosphine-Catalyzed [3 + 2] Cyclization of Allenoates and Enones: A Kinetic Shift toward Curtin-Hammett Control.The Journal of organic chemistry · 2025Article
- Asymmetric isochalcogenourea-catalysed (4 + 2)-cycloadditions ofOrganic & biomolecular chemistry · 2025Article
- Isochalcogenourea-catalyzed asymmetric (4 + 2)-heterocycloadditions of allenoates.Chemistry letters · 2024Article
- Enantioselective Syntheses of 3,4-Dihydropyrans Employing Isochalcogenourea-Catalyzed Formal (4+2)-Cycloadditions of Allenoates.Advanced synthesis & catalysis · 2024Article
- Chiral Isochalcogenourea-Catalysed Enantioselective (4+2) Cycloadditions of Allenoates.Angewandte Chemie (International ed. in English) · 2024Article
- Chiral Isochalcogenourea-Catalysed Enantioselective (4+2) Cycloadditions of Allenoates.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2024Article
- Multicomponent reaction (MCR) for constructingRSC advances · 2023Article
- Synthesis of tetrahydrochromenes and dihydronaphthofuransRSC advances · 2023Article
- Synthesis of fully functionalised spiropyran pyrazolone skeletonsRSC advances · 2022Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A regioselective [3+2] cyclisation reaction between 2-arylidene-1,3-indanedione and ethyl 2,3-butadienoate catalysed by triphenylphosphine has been demonstrated to synthesize functionalised spirocyclic cyclopentenes. The reaction tolerated various electron-rich and electron-deficient aryl substituted 2-arylidene-1,3-indanediones with high to excellent chemical yields (up to 99%) and moderate to good regioselectivity (up to 5 : 1). DFT studies have also been carried out to understand the regioselective nature of this reaction. The results of Frontier molecular orbital calculations and the activation energy (
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Registered trials
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