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

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Abstract

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

Graphical abstract: Revisiting the Juliá–Colonna enantioselective epoxidation: supramolecular catalysis in water

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Publication details

The article was received on 14 Feb 2017, accepted on 11 Apr 2017 and first published on 12 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC01168G
Citation: Chem. Commun., 2017, Advance Article
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    Revisiting the Juliá–Colonna enantioselective epoxidation: supramolecular catalysis in water

    C. Bérubé, X. Barbeau, P. Lagüe and N. Voyer, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC01168G

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