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Stereo- and chemodivergent NHC-promoted functionalisation of arylalkylketenes with chloral

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dc.contributor.authorDouglas, James
dc.contributor.authorChurchill, Gwydion
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorFox, David J.
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2015-09-28T08:40:03Z
dc.date.available2015-09-28T08:40:03Z
dc.date.issued2015-11-09
dc.identifier211274233
dc.identifier2e100f6f-a23d-411f-acc1-2dddfd28836b
dc.identifier84945903738
dc.identifier000365132100007
dc.identifier.citationDouglas , J , Churchill , G , Slawin , A M Z , Fox , D J & Smith , A D 2015 , ' Stereo- and chemodivergent NHC-promoted functionalisation of arylalkylketenes with chloral ' , Chemistry - A European Journal , vol. 21 , no. 46 , pp. 16354–16358 . https://doi.org/10.1002/chem.201503308en
dc.identifier.issn0947-6539
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567495
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861331
dc.identifier.urihttps://hdl.handle.net/10023/7548
dc.descriptionFunding: UK Engineering and Physical Sciences Research Council EP/G501742/1en
dc.description.abstractStereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to 88:12 dr, up to 94 % ee) or α-chloroesters (up to 94 % ee). Either 2-arylsubstitution or an α-branched iPr alkyl substituent within the ketene favours the chlorination pathway, allowing chloral to be used as an electrophilic chlorinating reagent in asymmetric catalysis.
dc.format.extent642506
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.subjectAsymmetric catalysisen
dc.subjectChlorination reactionsen
dc.subjectKetenesen
dc.subjectLactonesen
dc.subjectStereodivergent reactionsen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleStereo- and chemodivergent NHC-promoted functionalisation of arylalkylketenes with chloralen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doi10.1002/chem.201503308
dc.description.statusPeer revieweden
dc.identifier.urlhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201503308/suppinfoen
dc.identifier.grantnumberEP/D061768/1en
dc.identifier.grantnumberEP/K039210/1en


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