Crown-ether-modified cyclic dipeptides as supramolecular chiral catalysts

Authors: Bérubé, ChristopherVoyer, Normand
Abstract: With the objective to develop supramolecular catalysts for useful chemical transformations, we report here a rapid and efficient solid-phase synthesis of novel cyclic dipeptides (crown-CDPs) with a diversity of L-DOPA derived crown ether substituents and stereochemistry. We prepared and characterized 14 crown-CDPs and evaluated their efficiency as supramolecular epoxidation catalysts in a water/hexanes biphasic system. Yields increase significantly in the presence of the crown-CDPs, though enantioselectivity depends on the nature of the substituents. The results reported constitute a useful approach for chiral epoxides of interest and further illustrate the potential of cyclic peptides as supramolecular catalysts.
Document Type: Article de recherche
Issue Date: 20 October 2017
Open Access Date: 20 October 2018
Document version: AM
Permalink: http://hdl.handle.net/20.500.11794/31624
This document was published in: Supramolecular chemistry, Vol. 30 (3), 184–195 (2018)
https://doi.org/10.1080/10610278.2017.1392521
Gordon and Breach Science Publishers
Alternative version: 10.1080/10610278.2017.1392521
Collection:Articles publiés dans des revues avec comité de lecture

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