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Asymmetric synthesis of heterocyclic chloroamines and aziridines by enantioselective protonation of catalytically generated enamines

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dc.contributor.authorMcLean, Liam
dc.contributor.authorAshford, Matthew
dc.contributor.authorFyfe, Jamie
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorLeach, Andrew G.
dc.contributor.authorWatson, Allan J. B.
dc.date.accessioned2022-02-23T11:30:10Z
dc.date.available2022-02-23T11:30:10Z
dc.date.issued2022-03-16
dc.identifier277738307
dc.identifier61a94f1f-1504-4c87-ac0c-684897ba0035
dc.identifier000759392600001
dc.identifier85125056411
dc.identifier.citationMcLean , L , Ashford , M , Fyfe , J , Slawin , A M Z , Leach , A G & Watson , A J B 2022 , ' Asymmetric synthesis of heterocyclic chloroamines and aziridines by enantioselective protonation of catalytically generated enamines ' , Chemistry - A European Journal , vol. 28 , no. 16 , e202200060 . https://doi.org/10.1002/chem.202200060en
dc.identifier.issn0947-6539
dc.identifier.otherORCID: /0000-0002-9527-6418/work/108914284
dc.identifier.otherORCID: /0000-0002-1582-4286/work/108919064
dc.identifier.urihttps://hdl.handle.net/10023/24933
dc.descriptionL.A.M. and J.W.B.F. thank EPSRC for postdoctoral funding (EP/S027165/1; EP/R025754/1). J.W.B.F. thanks the Leverhulme Trust for postdoctoral funding (RPG-2018-362). M.W.A. thanks the University of St Andrews for a PhD studentship.en
dc.description.abstractWe report a method for the synthesis of chiral vicinal chloroamines via asymmetric protonation of catalytically generatedprochiral chloroenamines using chiral Brønsted acids. The processis highly enantioselective, with the origin of asymmetry and catalystsubstituent effects elucidated by DFT calculations. We show theutility of the method as an approach to the synthesis of a broadrange of heterocycle-substituted aziridines by treatment of thechloroamines with base in a one-pot process, as well as the utility ofthe process to allow access to vicinal diamines.
dc.format.extent6
dc.format.extent2207743
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.subjectAsymmetric catalysisen
dc.subjectAziridineen
dc.subjectBronstead aciden
dc.subjectChloroamineen
dc.subjectHeterocyclesen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subjectMCCen
dc.subject.lccQDen
dc.titleAsymmetric synthesis of heterocyclic chloroamines and aziridines by enantioselective protonation of catalytically generated enaminesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Leverhulme Trusten
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Sir James Mackenzie Institute for Early Diagnosisen
dc.identifier.doihttps://doi.org/10.1002/chem.202200060
dc.description.statusPeer revieweden
dc.identifier.urlhttps://doi.org/10.26434/chemrxiv-2021-d41h5en
dc.identifier.grantnumberEP/S027165/1en
dc.identifier.grantnumberEP/R025754/1en
dc.identifier.grantnumberRPG-7156en


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