Enantioselective copper catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent

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dc.contributor.authorShiely, Amy E.
dc.contributor.authorSlattery, Catherine N.
dc.contributor.authorFord, Alan
dc.contributor.authorEccles, Kevin S.
dc.contributor.authorLawrence, Simon E.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Councilen
dc.contributor.funderIrish Research Council for Science, Engineering and Technologyen
dc.contributor.funderEli Lilly and Companyen
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2017-03-24T09:31:13Z
dc.date.available2017-03-24T09:31:13Z
dc.date.issued2017-02-28
dc.date.updated2017-03-23T11:20:53Z
dc.description.abstractEnantioselectivities in C–H insertion reactions, employing the copper-bis(oxazoline)-NaBARF catalyst system, leading to cyclopentanones are highest with sulfonyl substituents on the carbene carbon, and furthermore, the impact is enhanced by increased steric demand on the sulfonyl substituent (up to 91%ee). Enantioselective intramolecular C–H insertion reactions of α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones are reported for the first time.en
dc.description.sponsorshipIrish Research Council (Project Number GOIPG/2013/1064); Irish Research Council for Science, Engineering and Technology, Eli Lilly (C. N. S) and Science Foundation Ireland (Grant Number 02/PICA/B802/EC07)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationShiely, A. E., Slattery, C. N., Ford, A., Eccles, K. S., Lawrence, S. E. and Maguire, A. R. (2017) ‘Enantioselective copper catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent’, Organic and Biomolecular Chemistry, 15, pp. 2609-2628. doi:10.1039/C7OB00214Aen
dc.identifier.doi10.1039/C7OB00214A
dc.identifier.endpage2628en
dc.identifier.issn1477-0520
dc.identifier.journaltitleOrganic and Biomolecular Chemistryen
dc.identifier.startpage2609en
dc.identifier.urihttps://hdl.handle.net/10468/3826
dc.identifier.volume15en
dc.language.isoenen
dc.rights© 2017, the Authors. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic and Biomolecular Chemistry. To access the final edited and published work see http://dx.doi.org/10.1039/C7OB00214Aen
dc.subjectC–H insertionen
dc.subjectCyclopentanoneen
dc.subjectSulfonyl substituenten
dc.titleEnantioselective copper catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituenten
dc.typeArticle (peer-reviewed)en
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