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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.identifier250962719
dc.identifier07670065-865e-41af-9c62-6aebd918224a
dc.identifier000412789600045
dc.identifier000412789600045
dc.identifier85032614861
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.otherORCID: /0000-0002-2104-7313/work/37255560
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861707
dc.identifier.urihttps://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.format.extent772046
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
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.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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