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Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/138417
Towards asymmetric catalysis by using tripodal pseudopeptidic cages
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The main goal of this project is the synthesis of a supramolecular pseudopeptidic cage that is
be able to recognize chloride ions (Figure 1). This recognition will later be proved for asymmetric
catalysis on different substrates. Three L-amino acids (phenylalanine) provide it the chiral centres
that should allow the cage to act as an asymmetric catalyst. The interest in this kind of catalysis
lies in getting enantiomerically enriched compounds, which have high synthetic interest and high
value, even though the reagents have affordable prizesIn order to get the desired cage (which will be called [1+1] because it is formed by one
aromatic electrophile and one tripodal amine) it is needed to use the template effect with the
chloride. Thanks to that, the third step of its synthesis (a SN2 reaction between a triple benzyl
bromide and a free triamine) will be promoted in a fully intramolecular way, yielding the desired
cage.
Finally, the cage has been characterized by 1H-NMR, 1H-1H (COSY), 13C-1H (HSQC) and by
ESI-MS, too. Thanks to these techniques it is possible to identify each proton and with whom it
interacts.
In the period available, different substrates were tested to try the asymmetric reactions
catalysed with the supramolecular cage. Finally, two reactions were studied: a β-chlorohydrine
cyclization to yield epoxides, and a β-chloroacid cyclization to yield β-lactones
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Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2019, Tutors: Tutors: Laura Rodríguez Raurell, Ciril Jimeno Mollet
Matèries (anglès)
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AQUINO SAMPER, Araceli de. Towards asymmetric catalysis by using tripodal pseudopeptidic cages. [consulta: 26 de gener de 2026]. [Disponible a: https://hdl.handle.net/2445/138417]