Chemical Communications, 2017, 53, 5099-5102.

Revisiting the Juliá-Colonna enantioselective epoxidation: supramolecular catalysis in water

Christopher BÉrubÉ, Xavier Barbeau, Patrick LagÜE, Normand Voyer


We 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 -helical structure and the presence of a hydrophobic groove of the homo-oligopeptide catalyst for reactivity and selectivity.

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Percée scientifique 2017 du journal Le Soleil

Compte rendu dans Chemical Communications Blog

Article dans le journal Le Fil

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