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Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones

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dc.contributor.authorYeh, Pei-Pei
dc.contributor.authorDaniels, David S. B.
dc.contributor.authorCordes, David B.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2015-01-16T00:01:32Z
dc.date.available2015-01-16T00:01:32Z
dc.date.issued2014-02-07
dc.identifier111957415
dc.identifier67e2437f-db93-4beb-a2dd-5e74a03892df
dc.identifier000331163900082
dc.identifier84893874366
dc.identifier000331163900082
dc.identifier.citationYeh , P-P , Daniels , D S B , Cordes , D B , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones ' , Organic Letters , vol. 16 , no. 3 , pp. 964-967 . https://doi.org/10.1021/ol403697hen
dc.identifier.issn1523-7060
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567514
dc.identifier.otherORCID: /0000-0002-5366-9168/work/28024033
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861777
dc.identifier.urihttps://hdl.handle.net/10023/6013
dc.descriptionThe authors thank the Royal Society for a University Research Fellowship (ADS) and the EPSRC (EP/J018139/1, DSBD) for funding.en
dc.description.abstractA one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.
dc.format.extent4
dc.format.extent700086
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.subjectBicyclic-Beta-Lactonesen
dc.subjectCatalyzed Aldol-Lactonizationen
dc.subjectAcyl Transfer Catalysten
dc.subjectAsymmetric-Synthesisen
dc.subjectDyotropic Rearrangementsen
dc.subjectNcal Reactionsen
dc.subjectKeto Acidsen
dc.subject3,5-dibromo-2-pyroneen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleIsothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyronesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Royal Societyen
dc.contributor.sponsorEPSRCen
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/ol403697h
dc.description.statusPeer revieweden
dc.date.embargoedUntil2015-01-16
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberUF090013en
dc.identifier.grantnumberEP/J018139/1en


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