Highly Selective Anion Template Effect in the Synthesis of Constrained Pseudopeptidic Macrocyclic Cyclophanes
| Autor: | M. Isabel Burguete, Belén Altava, Ferran Esteve, Michael Bolte, Eduardo García-Verdugo, Santiago V. Luis |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Substitution reaction
chlorine compounds anion template effects 010405 organic chemistry Organic Chemistry 010402 general chemistry Highly selective substitution reactions 01 natural sciences Chloride Combinatorial chemistry 0104 chemical sciences Ion Catalysis chemistry.chemical_compound chemistry Bromide scaffolds macrocyclic compounds medicine medicine.drug |
| Zdroj: | Repositori Universitat Jaume I Universitat Jaume I |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|