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Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes

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dc.contributor.authorSmith, Andrew David
dc.contributor.authorDavies, Alyn
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.date.accessioned2016-10-26T23:34:08Z
dc.date.available2016-10-26T23:34:08Z
dc.date.issued2015-12-14
dc.identifier228175618
dc.identifiereb991379-ddbc-41cc-8620-3255a2c30836
dc.identifier84955192735
dc.identifier000368282100011
dc.identifier.citationSmith , A D , Davies , A & Slawin , A M Z 2015 , ' Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes ' , Chemistry - A European Journal , vol. 21 , no. 52 , pp. 18944–18948 . https://doi.org/10.1002/chem.201504256en
dc.identifier.issn0947-6539
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567493
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861621
dc.identifier.urihttps://hdl.handle.net/10023/9709
dc.descriptionThe authors thank the Royal Society for a University Research Fellowship (A.D.S.), and the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no. 279850 (A.T.D.).en
dc.description.abstractThe N-heterocyclic carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated β-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.
dc.format.extent953545
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.subjectOrganocatalysisen
dc.subjectLewis-baseen
dc.subjectN-heterocyclic carbeneen
dc.subjectPentafluoroethylen
dc.subjectOxetaneen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleEnantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
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.doi10.1002/chem.201504256
dc.description.statusPeer revieweden
dc.date.embargoedUntil2016-10-26
dc.identifier.urlhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201504256/abstract#footer-support-infoen
dc.identifier.grantnumberEP/K039210/1en


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