Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides

Authors: Bérubé, ChristopherBarbeau, XavierCardinal, SébastienBoudreault, Pierre-LucBouchard, CorinneDelcey, NicolasLagüe, PatrickVoyer, Normand
Abstract: We 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.
Document Type: Article de recherche
Issue Date: 13 October 2016
Open Access Date: 11 October 2018
Document version: AM
This document was published in: Supramolecular chemistry, Vol.29 (5), 330-349 (2017)
Taylor & Francis group
Alternative version: 10.1080/10610278.2016.1236197
Collection:Articles publiés dans des revues avec comité de lecture

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