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Highly Selective Anion Template Effect in the Synthesis of Constrained Pseudopeptidic Macrocyclic Cyclophanes
dc.contributor.author | Esteve Franch, Ferran | |
dc.contributor.author | Altava, Belen | |
dc.contributor.author | Bolte, Michael | |
dc.contributor.author | Burguete, M. Isabel | |
dc.contributor.author | Garcia-Verdugo, Eduardo | |
dc.contributor.author | Luis, Santiago V. | |
dc.date.accessioned | 2020-03-10T10:37:29Z | |
dc.date.available | 2020-03-10T10:37:29Z | |
dc.date.issued | 2019-12-20 | |
dc.identifier.citation | ESTEVE, Ferran, et al. Highly selective anion template effect in the synthesis of constrained pseudopeptidic macrocyclic cyclophanes. The Journal of Organic Chemistry, 2019, 85.2: 1138-1145. | ca_CA |
dc.identifier.uri | http://hdl.handle.net/10234/186943 | |
dc.description.abstract | Herein, we report the synthesis of a novel family of constrained pseudopeptidic macrocyclic compounds containing the hexahydropyrrolo[3,4-f]isoindolocyclophane scaffold and involving four coupled substitution reactions in the macrocyclization process. Although the increase in the number of steps involved in the macrocyclization could lead to a larger number of possible side products, the optimization of the methodology and the study of the driving forces have made it possible to obtain the desired macrocycles in excellent yields. A thorough computational study has been carried out to understand the macrocyclization process, and the results obtained nicely agree with experimental data. Moreover, the bromide anion had a clear catalytic template effect in the macrocyclization reaction, and surprisingly, the chloride anion had a negative template effect in opposition to the results obtained for analogous macrocycles. The parameters responsible for the specific kinetic template effect observed have been studied in detail. | ca_CA |
dc.format.extent | 8 p. | ca_CA |
dc.format.mimetype | application/pdf | ca_CA |
dc.language.iso | eng | ca_CA |
dc.publisher | American Chemical Society | ca_CA |
dc.rights | Copyright © 2019 American Chemical Society | ca_CA |
dc.rights.uri | http://rightsstatements.org/vocab/InC/1.0/ | * |
dc.subject | chlorine compounds | ca_CA |
dc.subject | scaffolds | ca_CA |
dc.subject | substitution reactions | ca_CA |
dc.subject | anion template effects | ca_CA |
dc.subject | macrocyclic compounds | ca_CA |
dc.title | Highly Selective Anion Template Effect in the Synthesis of Constrained Pseudopeptidic Macrocyclic Cyclophanes | ca_CA |
dc.type | info:eu-repo/semantics/article | ca_CA |
dc.identifier.doi | https://doi.org/10.1021/acs.joc.9 | |
dc.relation.projectID | Spanish Ministry of Education, Culture and Sports (RTI2018-098233-B-C22 and predoctoral fellowship (FPU/2017/02060)) ; Generalitat Valenciana (PROMETEO/2016/071) ; | ca_CA |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | ca_CA |
dc.relation.publisherVersion | https://pubs.acs.org/doi/abs/10.1021/acs.joc.9b03048 | ca_CA |
dc.date.embargoEndDate | 2020-12-20 | |
dc.type.version | info:eu-repo/semantics/acceptedVersion | ca_CA |
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