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Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst

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dc.contributor.authorBarrios Antunez, Diego Javier
dc.contributor.authorGreenhalgh, Mark David
dc.contributor.authorFallan, Charlene
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2017-06-30T23:36:40Z
dc.date.available2017-06-30T23:36:40Z
dc.date.issued2016-08-14
dc.identifier.citationBarrios Antunez , D J , Greenhalgh , M D , Fallan , C , Slawin , A M Z & Smith , A D 2016 , ' Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst ' , Organic & Biomolecular Chemistry , vol. 14 , no. 30 , pp. 7268-7274 . https://doi.org/10.1039/C6OB01326Ken
dc.identifier.issn1477-0520
dc.identifier.otherPURE: 243749612
dc.identifier.otherPURE UUID: 616371c2-f1f8-42ee-9ae5-0fd64a26c21b
dc.identifier.otherScopus: 84979879918
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567488
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861898
dc.identifier.otherWOS: 000381418900015
dc.identifier.urihttp://hdl.handle.net/10023/11129
dc.descriptionThe research leading to these results (D-J.B.A.; C. F.) has received funding from the ERC under the European Union's Seventh Framework Programme (FP7/2007-2013) / ERC grant agreement n° 279850. ADS thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractThe diastereo- and enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives (15 examples, up to 96:4 dr, 95:5 er) via intramolecular Michael addition has been developed using keto-enone substrates and a bifunctional tertiary amine-thiourea catalyst. This methodology was extended to include non-activated ketone pronucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.
dc.format.extent7
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.rightsCopyright 2016 the Authors. 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/10.1039/C6OB01326Ken
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleEnantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalysten
dc.typeJournal articleen
dc.contributor.sponsorEuropean Commissionen
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/10.1039/C6OB01326K
dc.description.statusPeer revieweden
dc.date.embargoedUntil2017-06-30
dc.identifier.grantnumberN/Aen


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