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Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols

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dc.contributor.authorHarrer, Siegfried
dc.contributor.authorGreenhalgh, Mark D.
dc.contributor.authorNeyyappadath, Rifahath M.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2020-07-09T23:34:21Z
dc.date.available2020-07-09T23:34:21Z
dc.date.issued2019-08
dc.identifier.citationHarrer , S , Greenhalgh , M D , Neyyappadath , R M & Smith , A D 2019 , ' Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols ' , Synlett , vol. 30 , no. 13 , pp. 1555-1560 . https://doi.org/10.1055/s-0037-1610721en
dc.identifier.issn0936-5214
dc.identifier.otherPURE: 259340008
dc.identifier.otherPURE UUID: 00c3f432-2168-424e-b620-5d825ce5faed
dc.identifier.otherORCID: /0000-0002-2104-7313/work/59464499
dc.identifier.otherScopus: 85070077654
dc.identifier.otherWOS: 000482516100009
dc.identifier.urihttps://hdl.handle.net/10023/20229
dc.descriptionAuthors thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1, R.M.N.) for funding. We thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850 (A.D.S.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractThe isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 mol% of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles that underpin this process are discussed, and selectivity factors for the individual kinetic resolution steps are reported in a model system.
dc.language.isoeng
dc.relation.ispartofSynletten
dc.rightsCopyright © Georg Thieme Verlag Stuttgart · New York 2019. 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://doi.org/10.1055/s-0037-1610721en
dc.subjectKinetic resolutionen
dc.subjectIsothioureaen
dc.subject(±)-1,2-diolsen
dc.subjectEnantioselective acylationen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleIsothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diolsen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.sponsorThe Royal Societyen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1055/s-0037-1610721
dc.description.statusPeer revieweden
dc.date.embargoedUntil2020-07-10
dc.identifier.grantnumberEP/L016419/1en
dc.identifier.grantnumberN/Aen
dc.identifier.grantnumberWM140071en


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