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CC BY 4.0 · SynOpen
DOI: 10.1055/a-2766-4857
paper

Light-Driven Stereoselective [2+2] Aryl Bisenones Cycloaddition: A Metal-Free Strategy for the Construction of Functionalized Pyrrolidines and Tetrahydrofurans

Authors

  • Francesca Franco 

    1   Chemistry department, University of Milan, Milano, Italy (Ringgold ID: RIN9304)

  • Tommaso Benettin

    2   Dipartimento di Chimica, Università degli Studi di Milano, Milan, Italy (Ringgold ID: RIN9304)

  • Fabrizio Medici

    3   Dipartimento di Chimica Organica e Industriale, Università degli studi di Milano, Milano, Italy

  • Sergio Rossi 

    4   Dipartimento di Chimica, Universita' degli Studi di Milano, Milano, Italy

  • Alessandra Puglisi

    5   Dipartimento di Chimica, Universita degli Studi di Milano, Milano, Italy (Ringgold ID: RIN9304)

  • Maurizio Benaglia 

    2   Dipartimento di Chimica, Università degli Studi di Milano, Milan, Italy (Ringgold ID: RIN9304)

Supported by: European Union -NextGenerationEU 1.5
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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 [2+2] cycloaddition promoted by catalytic amounts of Eosin Y, with Schreiner’s thiourea and Hantzsch ester acting as mediators under visible green light irradiation. The transformation showed to be 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.



Publication History

Received: 04 November 2025

Accepted after revision: 05 December 2025

Accepted Manuscript online:
05 December 2025

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