Personne : Barbeau, Xavier
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Barbeau
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Xavier
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Université Laval. Département de chimie
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ncf11891722
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Publication Accès libre Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides(Taylor & Francis group, 2016-10-13) Barbeau, Xavier; Delcey, Nicolas; Bérubé, Christopher; Cardinal, Sébastien; Bouchard, Corinne; Lagüe, Patrick; Boudreault, Pierre-Luc; Voyer, NormandWe synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.Publication Accès libre Revisiting the Juliá–Colonna enantioselective epoxidation : supramolecular catalysis in water(Royal Society of Chemistry, 2017-04-12) Barbeau, Xavier; Bérubé, Christopher; Lagüe, Patrick; Voyer, NormandWe describe an efficient epoxidation process leading to chiral epoxyketones using the reusable homo-oligopeptide poly-L-leucine (PLL) in pure water, without any organic co-solvent. A range of substituted epoxyketones can be accessed with good conversions and high enantioselectivities. Based on the experimental results and computational studies, we propose a mechanism that demonstrates the importance of both the α-helical structure and the presence of a hydrophobic groove of the homo-oligopeptide catalyst for reactivity and selectivity