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dc.contributor.authorLaunay, Guillaume G.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorO'Hagan, David
dc.date.accessioned2013-01-25T14:01:02Z
dc.date.available2013-01-25T14:01:02Z
dc.date.issued2010-04-26
dc.identifier16812319
dc.identifierd6784ffb-5593-4e8a-9b52-aed2d6d5c2a2
dc.identifier000277784900001
dc.identifier77952676644
dc.identifier.citationLaunay , G G , Slawin , A M Z & O'Hagan , D 2010 , ' Prins fluorination cyclisations : Preparation of 4-fluoro-pyran and -piperidine heterocycles ' , Beilstein Journal of Organic Chemistry , vol. 6 , 41 . https://doi.org/10.3762/bjoc.6.41en
dc.identifier.issn1860-5397
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861846
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281275
dc.identifier.urihttps://hdl.handle.net/10023/3333
dc.description.abstractThe Prins reaction was investigated using BF3 center dot OEt2 as a Lewis acid. It has been recently demonstrated, that if BF3 center dot OEt2 is used in stoichiometric amounts then these reactions generate fluorinated products where the BF3 center dot OEt2 contributes fluoride ion to quench the intermediate carbocations. In this study oxa- and aza-Prins reactions for the synthesis of 4-fluoro-pyrans and -piperidines were investigated. The products were obtained in good yields, but only with moderate diastereoselectivity. These Prins fluorination reactions can be accelerated under microwave conditions. The study extends the Prins fluorination methodology for the generation of the C-F bond in heterocycles.
dc.format.extent6
dc.format.extent334339
dc.language.isoeng
dc.relation.ispartofBeilstein Journal of Organic Chemistryen
dc.subject4-fluoropiperidineen
dc.subject4-fluoropyranen
dc.subjectHeterocyclesen
dc.subjectOrgano-fluorineen
dc.subjectChemistryen
dc.subjectPrins cyclisationen
dc.subjectExpeditious synthesisen
dc.subjectTetrahydropyransen
dc.subjectExchangeen
dc.subjectFacileen
dc.subjectEstersen
dc.subjectCopeen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titlePrins fluorination cyclisations : Preparation of 4-fluoro-pyran and -piperidine heterocyclesen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doi10.3762/bjoc.6.41
dc.description.statusPeer revieweden


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