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dc.contributor.authorBykova, Tanya
dc.contributor.authorAl-Maharik, Nawaf
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorO'Hagan, David
dc.date.accessioned2016-05-27T15:30:11Z
dc.date.available2016-05-27T15:30:11Z
dc.date.issued2016-01-21
dc.identifier236957926
dc.identifier7e5f0c9e-3972-4898-b209-c43b86f1d5c8
dc.identifier84983111469
dc.identifier000368687600035
dc.identifier.citationBykova , T , Al-Maharik , N , Slawin , A M Z & O'Hagan , D 2016 , ' Multicomponent reactions of methyl substituted all- cis tetrafluorocyclohexane aldehydes ' , Organic & Biomolecular Chemistry , vol. 14 , no. 3 , pp. 1117-1123 . https://doi.org/10.1039/C5OB02334Cen
dc.identifier.issn1477-0520
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861993
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281290
dc.identifier.urihttps://hdl.handle.net/10023/8889
dc.descriptionThe authors thank the EPSRC for supporting this work and DO’H is grateful for a Royal Society Wolfson Research Merit Award.en
dc.description.abstractThis paper reports the preparation of methyl substituted all-cis tetrafluorocyclohexanes prepared from a Birch reduction of benzoic acid, worked up with a methyl iodide quench. The resultant methylcyclohexadiene carboxylic acid was reduced to the alcohol and protected. The cyclohexadienyl ring was then epoxidised and the C-O bonds sequentially converted through deoxyfluorination reactions to two sets of isomers of all-cis tetrafluorocyclohexane isomers. Deprotection of the benzylic ether and then oxidation gave aldehydes which were then used in Ugi and Passerini multicomponent reactions, allowing this facially polarised cyclohexane to be incorporated into peptidic structural motifs.
dc.format.extent1309581
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleMulticomponent reactions of methyl substituted all-cis tetrafluorocyclohexane aldehydesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
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.doihttps://doi.org/10.1039/C5OB02334C
dc.description.statusPeer revieweden
dc.identifier.urlhttp://www.rsc.org/suppdata/c5/ob/c5ob02334c/c5ob02334c1.pdfen
dc.identifier.urlhttp://www.rsc.org/suppdata/c5/ob/c5ob02334c/c5ob02334c2.cifen
dc.identifier.grantnumberEP/L017911/1en
dc.identifier.grantnumberEP/F03055X/1en
dc.identifier.grantnumberEP/H022651/1en


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