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Synthesis 2021; 53(21): 4030-4041
DOI: 10.1055/a-1526-7839
DOI: 10.1055/a-1526-7839
feature
Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates
This work was sponsored by the Shanghai Pujiang Program (Grant No. 19PJ1402700), the Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, the National Natural Science Foundation of China (No. 22071059), and the East China Normal University (ECNU).
Abstract
A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C–C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.
Key words
carbocycles - heterocycles - ring expansion - Brønsted acid - synthetic methods - cyclopropanes - 2-pyronesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1526-7839.
- Supporting Information
Publikationsverlauf
Eingereicht: 19. Mai 2021
Angenommen nach Revision: 10. Juni 2021
Accepted Manuscript online:
10. Juni 2021
Artikel online veröffentlicht:
08. Juli 2021
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16 CCDC 2083287 (8n) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
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