Show simple item record

Files in this item

Thumbnail
Name:
Smith_2017_OrgLetters_Enantioselectve_AAM.pdf
Size:
753.9Kb
Format:
PDF
View/Open

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

Item metadata

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.doi10.1021/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


This item appears in the following Collection(s)

Show simple item record

Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.