2026-04-19T23:35:40Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/106442025-07-03T00:05:28Zcom_10259_3924com_10259_5086com_10259_2604col_10259_3925

Gómez Ayuso, Javier 767 600 0000-0002-5238-3248 Carreira Barral, Israel 763 600 0000-0002-4835-8752 Quesada Pato, Roberto 458 600 0000-0003-2764-7157 García Valverde, María 222 600 0000-0002-3990-8388 2025-07-02T08:08:52Z 2025-07-02T08:08:52Z 2025-05 1615-4150 https://hdl.handle.net/10259/10644 10.1002/adsc.202500166 1615-4169 Herein we present a novel one-pot methodology for the synthesis of enantioenriched 2H-pyrrolespirosuccinimides by copper-catalyzed reactions on Ugi adducts derived from enantiopure α-alkylbenzyl amines through a chirality transfer process. We have proposed a mechanism, supported by density functional theory (DFT) calculations, where a hydrogen radical-shuttle (HRS) process explains the chemical and stereochemical results. This work demonstrates the efficient stereoselective synthesis of structurally unique, highly functionalized nitrogen heterocyclic systems using simple protocols and affordable starting materials. We thank funding from MICIU/AEI/10.13039/501100011033 and ERDF, UE (grants PID2020-117610RB−I00 and PID2023-151848OB−I00) and Consejería de Educación de la Junta de Castilla y León and ERDF, UE (Project BU067P20). J. G.-A. thanks Consejería de Educación de la Junta de Castilla y León and ERDF, UE for his predoctoral and post-doctoral contracts. application/pdf eng Wiley Advanced Synthesis & Catalysis. 2025, e202500166 https://doi.org/10.1002/adsc.202500166 info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica, Técnica y de Innovación 2017-2020/PID2020-117610RB-I00/ES/SMALL MOLECULE TRANSMEMBRANE ANION CARRIERS FOR BIOLOGICAL APPLICATIONS/ info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica, Técnica y de Innovación 2021-2023/PID2023-151848OB-I00/ES/NUEVAS HERRAMIENTAS MOLECULARES PARA MANIPULAR LA HOMEOSTASIS/ info:eu-repo/grantAgreement/Junta de Castilla y León//BU067P20//Molecular tools targeting cellular metabolism for cancer therapy/ Attribution-NonCommercial-NoDerivatives 4.0 Internacional http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess Multicomponent reactions Radical reactions Copper catalys Succinimide Spirosuccinimide Spiro-2H-pyrrole Química orgánica Chemistry, Organic Asymmetric Synthesis of Highly Substituted Spiro[2H‐pyrrole‐2,3‐Succinimide] Derivatives by Copper‐Catalyzed Post‐Ugi Reactions info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Advanced Synthesis & Catalysis THUMBNAIL Gomez-asc_2025.pdf.jpg Gomez-asc_2025.pdf.jpg IM Thumbnail image/jpeg 4937 https://riubu.ubu.es/bitstream/10259/10644/6/Gomez-asc_2025.pdf.jpg 2eb89874f62f81235208180fdcd2a429 MD5 6 Gomez-asc_2025-sc_supporting_information.pdf.jpg Gomez-asc_2025-sc_supporting_information.pdf.jpg IM Thumbnail image/jpeg 3897 https://riubu.ubu.es/bitstream/10259/10644/7/Gomez-asc_2025-sc_supporting_information.pdf.jpg aac8fc3d628347e5d62c02061fcd4edf MD5 7 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/10644/4/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 4 CC-LICENSE license_rdf license_rdf application/rdf+xml; charset=utf-8 805 https://riubu.ubu.es/bitstream/10259/10644/3/license_rdf 4460e5956bc1d1639be9ae6146a50347 MD5 3 ORIGINAL Gomez-asc_2025.pdf Gomez-asc_2025.pdf application/pdf 4627970 https://riubu.ubu.es/bitstream/10259/10644/1/Gomez-asc_2025.pdf e65dcfddbe58971cabe664e2d4ffa71f MD5 1 Gomez-asc_2025-sc_supporting_information.pdf Gomez-asc_2025-sc_supporting_information.pdf Supporting information application/pdf 8935819 https://riubu.ubu.es/bitstream/10259/10644/5/Gomez-asc_2025-sc_supporting_information.pdf 0a0826a0ee3f8172c45225a9e428b673 MD5 5 10259/10644 oai:riubu.ubu.es:10259/10644 2025-07-03 02:05:28.094 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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