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Enantioselective NHC-catalyzed redox [4+2]-hetero-Diels-Alder reactions using α,β-unsaturated trichloromethyl ketones as amide equivalents

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dc.contributor.authorAttaba, Nassilia
dc.contributor.authorTaylor, James Edward
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2016-09-05T23:32:27Z
dc.date.available2016-09-05T23:32:27Z
dc.date.issued2015-10-02
dc.identifier.citationAttaba , N , Taylor , J E , Slawin , A M Z & Smith , A D 2015 , ' Enantioselective NHC-catalyzed redox [4+2]-hetero-Diels-Alder reactions using α,β-unsaturated trichloromethyl ketones as amide equivalents ' , The Journal of Organic Chemistry , vol. 80 , no. 19 , pp. 9728–9739 . https://doi.org/10.1021/acs.joc.5b01820en
dc.identifier.issn0022-3263
dc.identifier.otherPURE: 215164667
dc.identifier.otherPURE UUID: b9c18a07-5330-4b3a-91b4-83379e1b67fa
dc.identifier.otherScopus: 84942940694
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567497
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861706
dc.identifier.otherWOS: 000362386400036
dc.identifier.urihttp://hdl.handle.net/10023/9430
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 (N.A. and J.E.T.).en
dc.description.abstractα,β-Unsaturated trichloromethyl ketones are suitable α,β-unsaturated amide and ester equivalents in N-heterocyclic carbene (NHC)-catalyzed redox hetero-Diels-Alder reactions with azolium enolates generated from α-aroyloxyaldehydes. The initially formed syn-dihydropyranone products can be isolated, or can undergo ring-opening with benzylamine followed by aminolysis of the resulting CCl3 ketone to form a range of diamides with high diastereo- and enantioselectivity (up to >95:5 dr and >99% ee).
dc.language.isoeng
dc.relation.ispartofThe Journal of Organic Chemistryen
dc.rightsCopyright © 2015 American Chemical Society. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://dx.doi.org/10.1021/acs.joc.5b01820en
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleEnantioselective NHC-catalyzed redox [4+2]-hetero-Diels-Alder reactions using α,β-unsaturated trichloromethyl ketones as amide equivalentsen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.description.versionPostprinten
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.doihttps://doi.org/10.1021/acs.joc.5b01820
dc.description.statusPeer revieweden
dc.date.embargoedUntil2016-09-05
dc.identifier.urlhttp://pubsdc3.acs.org/doi/suppl/10.1021/acs.joc.5b01820en
dc.identifier.grantnumberEP/K031252/1en
dc.identifier.grantnumberEP/K039210/1en


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