Issue 37, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
14 feb. 2017
Accepted
11 apr. 2017
First published
12 apr. 2017

Chem. Commun., 2017,53, 5099-5102

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

C. Bérubé, X. Barbeau, P. Lagüe and N. Voyer, Chem. Commun., 2017, 53, 5099 DOI: 10.1039/C7CC01168G

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