Boron Dipyrromethene (BODIPY) as Electron-Withdrawing Group in Asymmetric Copper-Catalyzed [3+2] Cycloadditions for the Synthesis of Pyrrolidine-Based Biological Sensors

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dc.contributor.author Rigotti, Thomas
dc.contributor.author Asenjo-Pascual, Juan
dc.contributor.author Martín-Somer, Ana
dc.contributor.author Milán Rois, Paula
dc.contributor.author Cordani, Marco
dc.contributor.author Díaz-Tendero, Sergio
dc.contributor.author Somoza, Álvaro
dc.contributor.author Fraile, Alberto
dc.contributor.author Alemán, José
dc.contributor.other UAM. Departamento de Química es_ES
dc.contributor.other UAM. Departamento de Química Orgánica es_ES
dc.date.accessioned 2020-03-30T14:28:15Z
dc.date.available 2020-03-30T14:28:15Z
dc.date.issued 2020-03-17
dc.identifier.citation Advanced Synthesis and Catalysis 362.6 (2020): 1345-1355 en_US
dc.identifier.issn 1615-4169 es_ES
dc.identifier.uri http://hdl.handle.net/10486/690657
dc.description This is the peer reviewed version of the following article: Rigotti, T., Asenjo‐Pascual, J., Martín‐Somer, A., Milán Rois, P., Cordani, M., Díaz‐Tendero, S., ... & Alemán. Boron Dipyrromethene (BODIPY) as Electron‐Withdrawing Group in Asymmetric Copper‐Catalyzed [3+ 2] Cycloadditions for the Synthesis of Pyrrolidine‐Based Biological Sensors. Advanced Synthesis & Catalysis Volume 362, Issue 6, 17 March 2020, Pages 1345-1355 , which has been published in final form at https://doi.org/10.1002/adsc.201901465. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions en_US
dc.description.abstract In this work, we describe the use of Boron Dipyrromethene (BODIPY) as electron-withdrawing group for activation of double bonds in asymmetric copper-catalyzed [3+2] cycloaddition reactions with azomethine ylides. The reactions take place under smooth conditions and with high enantiomeric excess for a large number of different substituents, pointing out the high activation of the alkene by using a boron dipyrromethene as electron-withdrawing group. Experimental, theoretical studies and comparison with other common electron-withdrawing groups in asymmetric copper-catalyzed [3+2] cycloadditions show the reasons of the different reactivity of the boron dipyrromethene derivatives, which can be exploited as a useful activating group in asymmetric catalysis. Additional experiments show that the so obtained pyrrolidines can be employed as biocompatible biosensors, which can be located in the endosomal compartments and do not present toxicity in three cell lines en_US
dc.description.sponsorship This work was supported by the Spanish Government (RTI2018‐095038‐B‐I00, CTQ2016‐76061‐P, SAF2017‐87305‐R), Comunidad de Madrid (IND2017/IND‐7809), and co‐financed by European Structural and Investment Fund. We acknowledge the generous allocation of computing time at the CCC (UAM). Financial support from the Spanish Ministry of Economy and Competitiveness, through the ‘‘Maria de Maeztu’’ Program of Excellence in R&D (MDM‐2014‐0377), is also acknowledged. Asociación Española Contra el Cáncer, and IMDEA Nanociencia acknowledge support from the ′Severo Ochoa′ Programme for Centres of Excellence in R&D (MINECO, Grant SEV‐2016‐0686). P.M.R thanks the Ministry of Economy, Industry and competitiveness of Spain for the FPI grant (BES‐2017.082521). A.M.S. thanks CAM for a postdoctoral contract (2016‐T2/IND‐1660) en_US
dc.format.extent 12 pag. en_US
dc.format.mimetype application/pdf en
dc.language.iso eng en
dc.publisher Wiley - VCH Verlag GmbH & Co. KGaA en_US
dc.relation.ispartof Advanced Synthesis and Catalysis en_US
dc.rights © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim en_US
dc.subject.other BODIPY en_US
dc.subject.other Electron-Withdrawing Group en_US
dc.subject.other Frontier Molecular Orbitals en_US
dc.subject.other Asymmetric catalysis en_US
dc.subject.other Bioimaging cell en_US
dc.subject.other Cycloaddition en_US
dc.subject.other Pyrrolidines en_US
dc.title Boron Dipyrromethene (BODIPY) as Electron-Withdrawing Group in Asymmetric Copper-Catalyzed [3+2] Cycloadditions for the Synthesis of Pyrrolidine-Based Biological Sensors en_US
dc.type article en
dc.subject.eciencia Química es_ES
dc.date.embargoend 2021-03-17
dc.relation.publisherversion https://doi.org/10.1002/adsc.201901465 es_ES
dc.identifier.doi 10.1002/adsc.201901465 es_ES
dc.identifier.publicationfirstpage 1345 es_ES
dc.identifier.publicationissue 6 es_ES
dc.identifier.publicationlastpage 1355 es_ES
dc.identifier.publicationvolume 362 es_ES
dc.relation.projectID Gobierno de España. RTI2018‐095038‐B‐I00 es_ES
dc.relation.projectID Gobierno de España. CTQ2016‐76061‐P es_ES
dc.relation.projectID Gobierno de España. SAF2017‐87305‐R es_ES
dc.relation.projectID Gobierno de España. MDM‐2014‐0377 es_ES
dc.relation.projectID Gobierno de España. SEV‐2016‐0686 es_ES
dc.relation.projectID Gobierno de España. BES‐2017.082521 es_ES
dc.type.version info:eu-repo/semantics/acceptedVersion en
dc.rights.accessRights openAccess en
dc.authorUAM Martín Somer, Ana (264814)
dc.authorUAM Díaz-Tendero Victoria, Sergio (262857)
dc.authorUAM Fraile Carrasco, Alberto (258338)
dc.authorUAM Aleman Lara, José Julián (262855)


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