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Enantioselective synthesis of β-fluoro-β-aryl-α-amino pentenamides by organocatalytic [2,3]-sigmatropic rearrangement

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dc.contributor.authorKasten, Kevin
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2018-09-07T23:35:36Z
dc.date.available2018-09-07T23:35:36Z
dc.date.issued2017-10-06
dc.identifier.citationKasten , K , Slawin , A M Z & Smith , A D 2017 , ' Enantioselective synthesis of β-fluoro-β-aryl-α-amino pentenamides by organocatalytic [2,3]-sigmatropic rearrangement ' , Organic Letters , vol. 19 , no. 19 , pp. 5182-5185 . https://doi.org/10.1021/acs.orglett.7b02452en
dc.identifier.issn1523-7060
dc.identifier.otherPURE: 250962719
dc.identifier.otherPURE UUID: 07670065-865e-41af-9c62-6aebd918224a
dc.identifier.otherWOS: 000412789600045
dc.identifier.otherWOS: 000412789600045
dc.identifier.otherScopus: 85032614861
dc.identifier.otherORCID: /0000-0002-2104-7313/work/37255560
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861707
dc.identifier.urihttp://hdl.handle.net/10023/15992
dc.descriptionThe research leading to these results (K.K.) has received funding from the ERC under the European Union's Seventh Framework Programme (FP7/2007-2013) / ERC grant agreement n° 279850. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractThe tetramisole-promoted catalytic enantioselective [2,3]-sigmatropic rearrangement of quaternary ammonium salts bearing a (Z)-3-fluoro-3-arylprop-2-ene group generates, after addition of benzylamine, a range of β-fluoro-β-aryl-α-aminopentenamides containing a stereogenic tertiary fluorine substituent. Cyclic and acyclic nitrogen substituents as well as various aromatic substituents are tolerated, giving the β-fluoro-β-aryl-α-aminopentenamide products in up to 76% yield, 96:4 dr, and 98:2 er.
dc.format.extent4
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.rightsCopyright © 2017 American Chemical Society. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1021/acs.orglett.7b02452en
dc.subjectFlluorinated amino-acidsen
dc.subjectAllylic ammonium ylidesen
dc.subjectKinetic resolutionen
dc.subjectMedicinal chemistryen
dc.subjectProtein designen
dc.subjectCatalystsen
dc.subjectMannichen
dc.subjectBenzotetramisoleen
dc.subjectStraightforwarden
dc.subjectCycloadditionen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleEnantioselective synthesis of β-fluoro-β-aryl-α-amino pentenamides by organocatalytic [2,3]-sigmatropic rearrangementen
dc.typeJournal articleen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.sponsorThe Royal Societyen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1021/acs.orglett.7b02452
dc.description.statusPeer revieweden
dc.date.embargoedUntil2018-09-08
dc.identifier.urlhttp://pubs.acs.org/doi/suppl/10.1021/acs.orglett.7b02452en
dc.identifier.grantnumberN/Aen
dc.identifier.grantnumberWM140071en


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