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Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans

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dc.contributor.authorBelmessieri, D.
dc.contributor.authorDe La Houpliere, A.
dc.contributor.authorCalder, E.D.D.
dc.contributor.authorTaylor, J.E.
dc.contributor.authorSmith, A.D.
dc.date.accessioned2015-03-16T13:31:01Z
dc.date.available2015-03-16T13:31:01Z
dc.date.issued2014-07-28
dc.identifier.citationBelmessieri , D , De La Houpliere , A , Calder , E D D , Taylor , J E & Smith , A D 2014 , ' Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans ' , Chemistry - A European Journal , vol. 20 , no. 31 , pp. 9762-9769 . https://doi.org/10.1002/chem.201402684en
dc.identifier.issn0947-6539
dc.identifier.otherPURE: 159417548
dc.identifier.otherPURE UUID: d434bd90-639b-43ca-be84-34a619f7448b
dc.identifier.otherScopus: 84905659539
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567508
dc.identifier.otherWOS: 000340176600040
dc.identifier.urihttps://hdl.handle.net/10023/6248
dc.descriptionThe authors thank the Royal Society for a University Research Fellowship (A.D.S.), the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013), ERC Grant Agreement No. 279850 (A.D.L.H. and J.E.T.), and the EPSRC (DTA studentship to D.B.) for funding.en
dc.description.abstractA stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)-(-)-tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r. , 99% ee), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r., 99% ee). You can have it both ways! A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported, giving products with high d.r. and ee (see scheme).
dc.format.extent8
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.rights© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.subjectAsymmetric catalysisen
dc.subjectCinchona alkaloiden
dc.subjectIsothioureaen
dc.subjectMichael additionen
dc.subjectOrganocatalysisen
dc.subjectOxygen heterocyclesen
dc.subjectStereodivergenten
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleStereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofuransen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
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/10.1002/chem.201402684
dc.description.statusPeer revieweden


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