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 Yan 2017
Accepted
11 Dzi 2017
First published
12 Dzi 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements