Show simple item record

Files in this item


Item metadata

dc.contributor.authorTaylor, James E.
dc.contributor.authorDavies, Alyn T.
dc.contributor.authorDouglas, James J.
dc.contributor.authorChurchill, Gwydion
dc.contributor.authorSmith, Andrew D.
dc.identifier.citationTaylor , J E , Davies , A T , Douglas , J J , Churchill , G & Smith , A D 2017 , ' Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters ' , Tetrahedron: Asymmetry , vol. 28 , no. 2 , pp. 355-366 .
dc.identifier.otherPURE: 248972940
dc.identifier.otherPURE UUID: b2d93aad-b6c0-48f7-abe5-49f5adacc7ee
dc.identifier.otherRIS: urn:1B4613414D2B4613533C04355F63D790
dc.identifier.otherScopus: 85009811538
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567479
dc.identifier.otherWOS: 000395216200018
dc.descriptionThe authors thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 (J.E.T. and A.T.D.) as well as the EPSRC, UK and AstraZeneca plc, UK (Case award to J.J.D.) for financial support. A.D.S. thanks the Royal Society, London, UK, for a Wolfson Merit Award.en
dc.description.abstractN-Heterocyclic carbene (NHC)-catalysed redox [4+2]-hetero-Diels-Alder reactions of α-aroyloxyaldehydes with either β,γ-unsaturated α-ketoesters or α,β-unsaturated γ-ketoesters generates substituted syn-dihydropyranones in good yield with excellent enantioselectivity (up to >99:1 er). The product diastereoselectivity is markedly dependent upon the nature of the unsaturated enone substituent. The presence of either electron-neutral or electron-rich aryl substituents gives excellent diastereoselectivity (up to >99:5 dr), while electron-deficient aryl substituents give reduced diastereoselectivity. In these cases, the syn-dihydropyranone products are more susceptible to base-promoted epimerisation at the C(4)-position under the reaction conditions, accounting for the lower diastereoselectivity obtained.
dc.relation.ispartofTetrahedron: Asymmetryen
dc.rights© 2017 Published by Elsevier Ltd. This work has been 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-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoestersen
dc.typeJournal articleen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.sponsorThe Royal Societyen
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

This item appears in the following Collection(s)

Show simple item record