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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.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.otherPURE: 111957372
dc.identifier.otherPURE UUID: 62ce6294-1e12-4371-9686-a94fa6e04641
dc.identifier.otherWOS: 000331926900011
dc.identifier.otherScopus: 84894557755
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567512
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861688
dc.identifier.otherWOS: 000331926900011
dc.identifier.urihttp://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.language.isoeng
dc.relation.ispartofThe Journal of Organic Chemistryen
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © 2014 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see To access the final edited and published work see http://dx.doi.org/10.1021/jo402591ven
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.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/jo402591v
dc.description.statusPeer revieweden
dc.date.embargoedUntil2015-02-05
dc.identifier.grantnumberUF090013en


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