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DOI: 10.1055/a-2766-4857
Light-Driven Stereoselective Aryl Bisenone Cycloaddition: A Metal-Free Strategy for the Construction of Functionalized Pyrrolidines and Tetrahydrofurans
Autor*innen
This work was supported by: (a) MUSA - Multilayered Urban Sustainability Action – project, funded by the European Union – NextGenerationEU, under the National Recovery and Resilience Plan (NRRP) Mission 4 Component 2 Investment Line 1.5: Strengthening of research structures and creation of R&D ‘innovation ecosystems’, set up of ‘territorial leaders in R&D’; (b) PRIN 2022 grant ‘Enabling technologies for sustainable and innovative catalytic transformations - BEST-CAT’ (CUP G53D23003260006); (c) PSR 2025 grant ‘Catalytic approaches to the sustainable synthesis of high added-value fine chemicals’ by the Università degli Studi di Milano.
Abstract
In this study, we report an exploratory study on the reductive cyclization of nitrogen- and oxygen-containing aryl bisenones, enabling the efficient synthesis of highly functionalized pyrrolidines and tetrahydrofurans under visible light irradiation. The transformation proceeds through a photocatalytic cyclization promoted by catalytic amounts of Eosin Y, with Schreiner’s thiourea and Hantzsch ester acting as mediators under visible green light irradiation. The transformation is stereoselective and affords the five-membered heterocycle as a single, trans isomer. Moreover, the introduction of chiral oxazolidinone auxiliaries onto aryl bisenone precursors allowed the formation of chiral, highly substituted trans pyrrolidines and tetrahydrofurans in good yields, although with modest stereoselectivities.
Key words
photocatalysis - photocatalytic cyclization - Eosin Y - stereoselective synthesis - aryl bis-enones - pyrrolidines - tetrahydrofuransSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2766-4857.
- Supporting Information (PDF) (opens in new window)
Publikationsverlauf
Eingereicht: 04. November 2025
Angenommen nach Revision: 05. Dezember 2025
Accepted Manuscript online:
05. Dezember 2025
Artikel online veröffentlicht:
26. Januar 2026
© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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