Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides |
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Authors: | Christopher Bérubé Xavier Barbeau Sébastien Cardinal Pierre-Luc Boudreault Corinne Bouchard Nicolas Delcey |
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Institution: | 1. Département de Chimie and PROTEO, Université Laval, Québec, Canada;2. Département de Biochimie, Microbiologie et Bioinformatique and PROTéO, Université Laval, Québec, Canada |
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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. |
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Keywords: | Cyclic dipeptides interfacial epoxidation supramolecular catalysis |
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