Highly Selective Anion Template Effect in the Synthesis of Constrained Pseudopeptidic Macrocyclic Cyclophanes
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Título
Highly Selective Anion Template Effect in the Synthesis of Constrained Pseudopeptidic Macrocyclic CyclophanesAutoría
Fecha de publicación
2019-12-20Editor
American Chemical SocietyCita bibliográfica
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.Tipo de documento
info:eu-repo/semantics/articleVersión de la editorial
https://pubs.acs.org/doi/abs/10.1021/acs.joc.9b03048Versión
info:eu-repo/semantics/acceptedVersionPalabras clave / Materias
Resumen
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 ... [+]
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. [-]
Proyecto de investigación
Spanish Ministry of Education, Culture and Sports (RTI2018-098233-B-C22 and predoctoral fellowship (FPU/2017/02060)) ; Generalitat Valenciana (PROMETEO/2016/071) ;Derechos de acceso
Copyright © 2019 American Chemical Society
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