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Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids

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dc.contributor.authorMorrill, Louis C.
dc.contributor.authorSmith, Samuel M.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2015-02-05T00:01:45Z
dc.date.available2015-02-05T00:01:45Z
dc.date.issued2014-02-21
dc.identifier111957372
dc.identifier62ce6294-1e12-4371-9686-a94fa6e04641
dc.identifier000331926900011
dc.identifier84894557755
dc.identifier000331926900011
dc.identifier.citationMorrill , L C , Smith , S M , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids ' , The Journal of Organic Chemistry , vol. 79 , no. 4 , pp. 1640-1655 . https://doi.org/10.1021/jo402591ven
dc.identifier.issn0022-3263
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567512
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861688
dc.identifier.urihttps://hdl.handle.net/10023/6073
dc.descriptionThis work is supported by funding from the Carnegie Trust for the Universities of Scotland (L.C.M.) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013)/ERC Grant Agreement No. 279850.en
dc.description.abstractIsothiourea HBTM-2.1 promotes the catalytic asymmetric alpha-functionalization of 3-alkenoic acids through formal [2 + 2] cycloadditions with N-tosyl aldimines and formal [4 + 2] cycloadditions with either 4-aryltrifluoromethyl enones or N-aryl-N-aroyl diazenes, providing useful synthetic building blocks in good yield and with excellent enantiocontrol (up to >99% ee). Stereodefined products are amenable to further synthetic elaboration through manipulation of the olefinic functionality.
dc.format.extent16
dc.format.extent1577137
dc.language.isoeng
dc.relation.ispartofThe Journal of Organic Chemistryen
dc.subjectBicyclic-Beta-Lactonesen
dc.subjectEnantioselective Gamma-Aminationen
dc.subjectCarbonylative 2+2 Cycloadditionen
dc.subjectCatalyzed Aldol-Lactonizationen
dc.subjectPromoted Bis-Cyclizationsen
dc.subjectAcyl Transfer Catalysten
dc.subjectDelta-Lactonesen
dc.subjectDyotropic Rearrangementsen
dc.subjectEfficient Synthesisen
dc.subjectNcal Reactionsen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleIsothiourea-mediated asymmetric functionalization of 3-alkenoic acidsen
dc.typeJournal articleen
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/jo402591v
dc.description.statusPeer revieweden
dc.date.embargoedUntil2015-02-05
dc.identifier.grantnumberUF090013en


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