Chemical Communications, 2017, 53, 5099-5102.
Revisiting the Juliá-Colonna enantioselective epoxidation: supramolecular catalysis in water
Christopher BÉrubÉ, Xavier Barbeau, Patrick LagÜE, Normand Voyer
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 -helical structure and the presence of a hydrophobic groove of the homo-oligopeptide catalyst for reactivity and selectivity.
In the press:
Percée scientifique 2017 du journal Le Soleil
Compte rendu dans Chemical Communications Blog
Article dans le journal Le Fil
Nouvelle sur le site de la FSG