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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.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 .
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.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.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:
dc.subjectQD Chemistryen
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.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.description.statusPeer revieweden

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