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dc.contributor.authorBykova, Tetiana
dc.contributor.authorAl-Maharik, Nawaf
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorO'Hagan, David
dc.identifier.citationBykova , T , Al-Maharik , N , Slawin , A M Z & O'Hagan , D 2017 , ' Fluorinated cyclohexanes : synthesis of amine building blocks of the all-cis 2,3,5,6-tetrafluorocyclohexylamine motif ' , Beilstein Journal of Organic Chemistry , vol. 13 , pp. 728-733 .
dc.identifier.otherPURE: 250026750
dc.identifier.otherPURE UUID: 8f730f96-a53e-4038-8bff-5358833e0560
dc.identifier.otherRIS: urn:FF6A62430192600091901BF20271102D
dc.identifier.otherScopus: 85020761241
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861810
dc.identifier.otherWOS: 000407577200001
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281265
dc.description.abstractThis paper reports the synthesis of three amine stereoisomers 5a–c of the tetrafluorocyclohexyl ring system, as building blocks for discovery chemistry programmes. The synthesis starts from a Birch reduction of benzonitrile, followed by an in situ methyl iodide quench. The resultant 2,5-cyclohexadiene was progressed via double epoxidations and then hydrofluorination ring opening reactions. The resultant fluorohydrin moieties were then converted to different stereoisomers of the tetrafluorocyclohexyl ring system, and then reductive hydrogenation of the nitrile delivered three amine stereoisomers. It proved necessary to place a methyl group on the cyclohexane ring in order to stabilise the compound against subsequent HF elimination. The two all-cis tetrafluorocyclohexyl isomers 5a and 5b constitute facially polarized cyclohexane rings, with fluorines on the electronegative face and hydrogens on the electropositive face.
dc.relation.ispartofBeilstein Journal of Organic Chemistryen
dc.rights© 2017 Bykova et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.en
dc.subjectAll-cis tetrafluorocyclohexane motifen
dc.subjectDeoxofluorination reactionsen
dc.subjectFluorinated aminesen
dc.subjectFluorinated cyclohexanesen
dc.subjectQD Chemistryen
dc.titleFluorinated cyclohexanes : synthesis of amine building blocks of the all-cis 2,3,5,6-tetrafluorocyclohexylamine motifen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
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.description.statusPeer revieweden

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