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Catalytic enantioselective synthesis of α-chiral azaheteroaryl ethylamines by asymmetric protonation
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dc.contributor.author | Xu, Chao | |
dc.contributor.author | Muir, Calum | |
dc.contributor.author | Leach, Andrew | |
dc.contributor.author | Kennedy, Alan | |
dc.contributor.author | Watson, Allan J. B. | |
dc.date.accessioned | 2019-07-31T23:41:32Z | |
dc.date.available | 2019-07-31T23:41:32Z | |
dc.date.issued | 2018-08-01 | |
dc.identifier | 254052956 | |
dc.identifier | 43fb85b1-7027-42fa-887e-89ffa37e85bf | |
dc.identifier | 85051871936 | |
dc.identifier | 000442340000046 | |
dc.identifier.citation | Xu , C , Muir , C , Leach , A , Kennedy , A & Watson , A J B 2018 , ' Catalytic enantioselective synthesis of α-chiral azaheteroaryl ethylamines by asymmetric protonation ' , Angewandte Chemie International Edition , vol. In press . https://doi.org/10.1002/anie.201806956 | en |
dc.identifier.issn | 1433-7851 | |
dc.identifier.other | ORCID: /0000-0002-1582-4286/work/56639173 | |
dc.identifier.uri | https://hdl.handle.net/10023/18223 | |
dc.description | The authors thank the Leverhulme Trust for funding (C.X.; RPG-2015- 308) and GSK for a PhD studentship (C.W.M.). The authors thank the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses. | en |
dc.description.abstract | The direct enantioselective synthesis of chiral azaheteroaryl ethylamines from vinyl‐substituted N‐heterocycles and anilines is reported. A chiral phosphoric acid (CPA) catalyst promotes dearomatizing aza‐Michael addition to give a prochiral exocyclic aryl enamine, which undergoes asymmetric protonation upon rearomatization. The reaction accommodates a broad range of N‐heterocycles, nucleophiles, and substituents on the prochiral centre, generating the products in high enantioselectivity. DFT studies support a facile nucleophilic addition based on catalyst‐induced LUMO lowering, with site‐selective, rate‐limiting, intramolecular asymmetric proton transfer from the ion‐paired prochiral intermediate. | |
dc.format.extent | 1628800 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie International Edition | en |
dc.subject | Asymmetric catalysis | en |
dc.subject | Brønsted acid | en |
dc.subject | DFT | en |
dc.subject | Heterocycles | en |
dc.subject | Stereochemistry | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Catalytic enantioselective synthesis of α-chiral azaheteroaryl ethylamines by asymmetric protonation | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Leverhulme Trust | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1002/anie.201806956 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-08-01 | |
dc.identifier.grantnumber | RPG-2015-308 | en |
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