Organocatalytic asymmetric peroxidation of g,d-unsaturated ß-keto esters - A novel route to chiral cycloperoxides

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dc.contributor.authorHennessy, Mary C.
dc.contributor.authorHirenkumar, Gandhi
dc.contributor.authorO'Sullivan, Timothy P.
dc.contributor.funderIrish Research Council
dc.contributor.funderScience Foundation Ireland
dc.date.accessioned2023-10-16T15:57:00Z
dc.date.available2023-10-16T15:09:07Zen
dc.date.available2023-10-16T15:57:00Z
dc.date.issued2023-05-24
dc.date.updated2023-10-16T14:09:11Zen
dc.description.abstractA methodology for the asymmetric peroxidation of g,d-unsaturated ß-keto esters is presented. Using a cinchona-derived organocatalyst, the target d-peroxy-ß-keto esters were obtained in high enantiomeric ratios of up to 95:5. Additionally, these d-peroxy esters can be readily reduced to chiral d-hydroxy-ß-keto esters without impacting the ß-keto ester functionality. Importantly, this chemistry opens up a concise route to chiral 1,2-dioxolanes, a common motif in many bioactive natural products, via a novel P2O5-mediated cyclisation of the corresponding d-peroxy-ß-hydroxy esters.en
dc.description.sponsorshipIrish Research Council (PhD scholarships (GOIPG/2018/496), (GOIPG/2013/113))
dc.description.statusPeer revieweden
dc.description.versionPublished Version
dc.format.mimetypeapplication/pdfen
dc.identifier.articleid4317
dc.identifier.citationHennessy, M.C., Gandhi, H. and O’Sullivan, T.P. (2023) ‘Organocatalytic asymmetric peroxidation of γ,δ-unsaturated β-keto esters—a novel route to chiral cycloperoxides’, Molecules, 28(11), 4317 (12 pp). https://doi.org/10.3390/molecules28114317.
dc.identifier.doi10.3390/molecules28114317en
dc.identifier.endpage12
dc.identifier.issn1420-3049
dc.identifier.issued11
dc.identifier.journaltitleMolecules
dc.identifier.startpage1
dc.identifier.urihttps://hdl.handle.net/10468/15121
dc.identifier.volume28
dc.language.isoenen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/15/RI/3221/IE/Process Flow Spectroscopy (ProSpect); Advanced Reaction Understanding using Flow Nuclear Magnetic Resonance (NMR) and Infrared (IR) Spectroscopies, with On-Line Ultra-Performance Liquid Chromatography (UPLC) and Mass Spectrometry (MS)/
dc.relation.urihttps://doi.org/10.3390/molecules28114317
dc.rights© 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectCycloperoxides
dc.subjectOrganocatalysis
dc.subjectδ-peroxy-β-keto esters
dc.subjectδ-hydroxy-β-keto esters
dc.subject1,2-dioxolanes
dc.titleOrganocatalytic asymmetric peroxidation of g,d-unsaturated ß-keto esters - A novel route to chiral cycloperoxidesen
dc.typeArticle (peer-reviewed)
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