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alpha-Ketophosphonates as ester surrogates : isothiourea-catalyzed asymmetric diester and lactone synthesis

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dc.contributor.authorSmith, Siobhan R.
dc.contributor.authorLeckie, Stuart M.
dc.contributor.authorHolmes, Reuben
dc.contributor.authorDouglas, James
dc.contributor.authorFallan, Charlene
dc.contributor.authorShapland, Peter
dc.contributor.authorPryde, David
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2015-04-14T23:01:41Z
dc.date.available2015-04-14T23:01:41Z
dc.date.issued2014-05-02
dc.identifier134757706
dc.identifiera25bc37a-2545-45a5-b109-2762f5b35571
dc.identifier000335491000053
dc.identifier84899825801
dc.identifier000335491000053
dc.identifier.citationSmith , S R , Leckie , S M , Holmes , R , Douglas , J , Fallan , C , Shapland , P , Pryde , D , Slawin , A M Z & Smith , A D 2014 , ' alpha-Ketophosphonates as ester surrogates : isothiourea-catalyzed asymmetric diester and lactone synthesis ' , Organic Letters , vol. 16 , no. 9 , pp. 2506-2509 . https://doi.org/10.1021/ol500873sen
dc.identifier.issn1523-7060
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567510
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861933
dc.identifier.urihttps://hdl.handle.net/10023/6480
dc.descriptionThis work is in part supported by the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850en
dc.description.abstractIsothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using α-keto-β,γ-unsaturated phosphonates as α,β-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or enantioenriched functionalized diesters upon ring-opening.
dc.format.extent4
dc.format.extent970407
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.subjectBicyclic-beta-lactonesen
dc.subjectBis(oxazolinyl)pyridine-scandium(III) triflate complexesen
dc.subjectFriedel-Crafts alkylationsen
dc.subjectAcyl transfer catalysten
dc.subjectDiels-Alder reactionsen
dc.subjectAldol-Lactonizationen
dc.subjectDyotropic Rearrangementsen
dc.subjectKeto Acidsen
dc.subjectOrganocatalysisen
dc.subjectMichaelen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titlealpha-Ketophosphonates as ester surrogates : isothiourea-catalyzed asymmetric diester and lactone synthesisen
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/ol500873s
dc.description.statusPeer revieweden
dc.date.embargoedUntil2015-04-15
dc.identifier.grantnumberUF090013en


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