Copper mediated, heterogeneous, enantioselective intramolecular Buchner reactions of a-diazoketones using continuous flow processing

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dc.contributor.authorCrowley, Daniel C.
dc.contributor.authorLynch, Denis
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Councilen
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderEuropean Regional Development Funden
dc.date.accessioned2018-03-23T15:51:24Z
dc.date.available2018-03-23T15:51:24Z
dc.date.issued2018-03-15
dc.date.updated2018-03-23T15:39:04Z
dc.description.abstractEnantioselective intramolecular Buchner reactions of α-diazoketones can be effected using heterogeneous copper−bis(oxazoline) catalysts in batch or using continuous flow processing in up to 83% ee. The catalyst can be reused up to 7 times without loss of activity. For α-diazoketones 3 and 4, the enantioselection achieved in flow with the immobilized catalyst was comparable with the standard homogeneous catalyzed process.en
dc.description.sponsorshipIrish Research Council (GOIPG/2015/2972);en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationCrowley, D. C., Lynch, D. and Maguire, A. R. (2018) 'Copper mediated, heterogeneous, enantioselective intramolecular Buchner reactions of α-diazoketones using continuous flow processing', The Journal of Organic Chemistry, In Press, doi: 10.1021/acs.joc.8b00147en
dc.identifier.doi10.1021/acs.joc.8b00147
dc.identifier.endpage24en
dc.identifier.issn0022-3263
dc.identifier.journaltitleThe Journal of Organic Chemistryen
dc.identifier.startpage1en
dc.identifier.urihttps://hdl.handle.net/10468/5689
dc.language.isoenen
dc.publisherAmerican Chemical Societyen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
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)/en
dc.rights© 2017 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.joc.8b00147en
dc.subjectBuchner reactionsen
dc.subjectCatalystsen
dc.subjectα-diazoketonesen
dc.subjectContinuous flow processingen
dc.titleCopper mediated, heterogeneous, enantioselective intramolecular Buchner reactions of a-diazoketones using continuous flow processingen
dc.typeArticle (peer-reviewed)en
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