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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.identifier243749612
dc.identifier616371c2-f1f8-42ee-9ae5-0fd64a26c21b
dc.identifier84979879918
dc.identifier000381418900015
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.otherORCID: /0000-0002-2104-7313/work/36567488
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861898
dc.identifier.urihttps://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.format.extent1164587
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
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.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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