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

dc.check.date2019-03-15
dc.check.infoAccess to this article is restricted until 12 months after publication by request of the publisher.en
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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