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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.author | Attaba, Nassilia | |
dc.contributor.author | Taylor, James Edward | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2016-09-05T23:32:27Z | |
dc.date.available | 2016-09-05T23:32:27Z | |
dc.date.issued | 2015-10-02 | |
dc.identifier | 215164667 | |
dc.identifier | b9c18a07-5330-4b3a-91b4-83379e1b67fa | |
dc.identifier | 84942940694 | |
dc.identifier | 000362386400036 | |
dc.identifier.citation | Attaba , 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.5b01820 | en |
dc.identifier.issn | 0022-3263 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567497 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861706 | |
dc.identifier.uri | https://hdl.handle.net/10023/9430 | |
dc.description | The 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.abstract | α,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.format.extent | 1370284 | |
dc.language.iso | eng | |
dc.relation.ispartof | The Journal of Organic Chemistry | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Enantioselective NHC-catalyzed redox [4+2]-hetero-Diels-Alder reactions using α,β-unsaturated trichloromethyl ketones as amide equivalents | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1021/acs.joc.5b01820 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2016-09-05 | |
dc.identifier.url | http://pubsdc3.acs.org/doi/suppl/10.1021/acs.joc.5b01820 | en |
dc.identifier.grantnumber | EP/K031252/1 | en |
dc.identifier.grantnumber | EP/K039210/1 | en |
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