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Synthesis 2024; 56(12): 1912-1922
DOI: 10.1055/s-0042-1751563
DOI: 10.1055/s-0042-1751563
paper
Divergent Reactivity of δ-Acetoxy Allenoates with 1,3-Bisnucleophiles: Synthesis of Multisubstituted Pyran, Dihydropyran, and 3-Vinylpent-2-enedioate Scaffolds
K.C.K. thanks SERB for a J. C. Bose fellowship (JBR/2020/000038) for funding. We also thank partial support from IoE (University of Hyderabad).
Abstract
Base-dependent synthesis of tetrasubstituted pyrans or 3,4-dihydropyrans using δ-acetoxy allenoates and enolizable carbonyls like cyclohexan-1,3-dione and ethyl benzoylacetate is reported. Thus, the use of DMAP as an organocatalytic base gives tetrasubstituted pyrans while DBU affords isomeric tetrasubstituted 3,4-dihydropyrans. The reaction of δ-acetoxy allenoates with ethyl benzoylacetate mediated by KO t Bu furnishes diethyl 3-vinylpent-2-enedioates.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751563.
- Supporting Information
Publikationsverlauf
Eingereicht: 14. Dezember 2023
Angenommen nach Revision: 05. Februar 2024
Artikel online veröffentlicht:
20. Februar 2024
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For reviews, see:
For selected NHC/amine-catalyzed reactions, see:
For selected phosphine-catalyzed reactions, see:
Annulations via diene-ammonium ion:
Annulations via diene-phosphonium ion: