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Asymmetric synthesis of heterocyclic chloroamines and aziridines by enantioselective protonation of catalytically generated enamines
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dc.contributor.author | McLean, Liam | |
dc.contributor.author | Ashford, Matthew | |
dc.contributor.author | Fyfe, Jamie | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Leach, Andrew G. | |
dc.contributor.author | Watson, Allan J. B. | |
dc.date.accessioned | 2022-02-23T11:30:10Z | |
dc.date.available | 2022-02-23T11:30:10Z | |
dc.date.issued | 2022-03-16 | |
dc.identifier | 277738307 | |
dc.identifier | 61a94f1f-1504-4c87-ac0c-684897ba0035 | |
dc.identifier | 000759392600001 | |
dc.identifier | 85125056411 | |
dc.identifier.citation | McLean , 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.202200060 | en |
dc.identifier.issn | 0947-6539 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/108914284 | |
dc.identifier.other | ORCID: /0000-0002-1582-4286/work/108919064 | |
dc.identifier.uri | https://hdl.handle.net/10023/24933 | |
dc.description | L.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.abstract | We 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.extent | 6 | |
dc.format.extent | 2207743 | |
dc.language.iso | eng | |
dc.relation.ispartof | Chemistry - A European Journal | en |
dc.subject | Asymmetric catalysis | en |
dc.subject | Aziridine | en |
dc.subject | Bronstead acid | en |
dc.subject | Chloroamine | en |
dc.subject | Heterocycles | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | MCC | en |
dc.subject.lcc | QD | en |
dc.title | Asymmetric synthesis of heterocyclic chloroamines and aziridines by enantioselective protonation of catalytically generated enamines | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | The Leverhulme Trust | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Sir James Mackenzie Institute for Early Diagnosis | en |
dc.identifier.doi | https://doi.org/10.1002/chem.202200060 | |
dc.description.status | Peer reviewed | en |
dc.identifier.url | https://doi.org/10.26434/chemrxiv-2021-d41h5 | en |
dc.identifier.grantnumber | EP/S027165/1 | en |
dc.identifier.grantnumber | EP/R025754/1 | en |
dc.identifier.grantnumber | RPG-7156 | en |
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