Exploiting continuous processing for challenging diazo transfer and telescoped copper-catalyzed asymmetric transformations

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dc.contributor.authorCrowley, Daniel C.
dc.contributor.authorBrouder, Thomas A.
dc.contributor.authorKearney, Aoife M.
dc.contributor.authorLynch, Denis
dc.contributor.authorFord, Alan
dc.contributor.authorCollins, Stuart G.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Councilen
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderEuropean Regional Development Funden
dc.date.accessioned2021-08-12T07:52:46Z
dc.date.available2021-08-12T07:52:46Z
dc.date.issued2021-08-11
dc.date.updated2021-08-12T07:36:45Z
dc.description.abstractGeneration and use of triflyl azide in flow enables efficient synthesis of a range of α-diazocarbonyl compounds, including α-diazoketones, α-diazoamides, and an α-diazosulfonyl ester, via both Regitz-type diazo transfer and deacylative/debenzoylative diazo-transfer processes with excellent yields and offers versatility in the solvent employed, in addition to addressing the hazards associated with handling of this highly reactive sulfonyl azide. Telescoping the generation of triflyl azide and diazo-transfer process with highly enantioselective copper-mediated intramolecular aromatic addition and C–H insertion processes demonstrates that the reaction stream containing the α-diazocarbonyl compound can be obtained in sufficient purity to pass directly over the immobilized copper bis(oxazoline) catalyst without detrimentally impacting the catalyst enantioselectivity.en
dc.description.sponsorshipIrish Research Council (GOIPG/2015/2972; GOIPG/2015/3188; GOIPG/2018/112); Science Foundation Ireland (SFI SSPC2 12/RC/22755 and SFI SSPC3 Pharm5 12/RC/2275_2; SFI 15/RI/3221)en
dc.description.statusPeer revieweden
dc.description.versionPublished Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationCrowley, D. C., Brouder, T. A., Kearney, A. M., Lynch, D., Ford, A., Collins, S. G. and Maguire, A. R. (2021) 'Exploiting continuous processing for challenging diazo transfer and telescoped copper-catalyzed asymmetric transformations', Journal of Organic Chemistry. doi: 10.1021/acs.joc.1c01310en
dc.identifier.doi10.1021/acs.joc.1c01310en
dc.identifier.eissn1520-6904
dc.identifier.issn0022-3263
dc.identifier.journaltitleJournal of Organic Chemistryen
dc.identifier.urihttps://hdl.handle.net/10468/11731
dc.language.isoenen
dc.publisherAmerican Chemical Societyen
dc.rights© 2021, the Authors. Published by American Chemical Society. This is an open access article under the terms of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).en
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/en
dc.subjectTriflyl azideen
dc.subjectRegitz-type diazo transferen
dc.subjectDeacylative/debenzoylative diazo transferen
dc.subjectα-diazocarbonyl compoundsen
dc.subjectα-diazoketonesen
dc.subjectα-diazoamidesen
dc.subjectα-diazosulfonyl esteren
dc.titleExploiting continuous processing for challenging diazo transfer and telescoped copper-catalyzed asymmetric transformationsen
dc.typeArticle (peer-reviewed)en
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