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dc.contributor.authorBrandolese, Arianna
dc.contributor.authorGreenhalgh, Mark David
dc.contributor.authorDesrues, Titouan
dc.contributor.authorLiu, Xueyang
dc.contributor.authorQu, Shen
dc.contributor.authorBressy, Cyril
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2021-04-01T15:30:01Z
dc.date.available2021-04-01T15:30:01Z
dc.date.issued2021-04-28
dc.identifier.citationBrandolese , A , Greenhalgh , M D , Desrues , T , Liu , X , Qu , S , Bressy , C & Smith , A D 2021 , ' Horeau amplification in the sequential acylative kinetic resolution of (±)-1,2-diols and (±)-1,3-diols in flow ' , Organic & Biomolecular Chemistry , vol. 19 , no. 16 , pp. 3620-3627 . https://doi.org/10.1039/D1OB00304Fen
dc.identifier.issn1477-0520
dc.identifier.otherPURE: 273232258
dc.identifier.otherPURE UUID: 92c8ba8b-96b9-43d1-81c8-c23c94cfef68
dc.identifier.otherORCID: /0000-0002-2104-7313/work/90567143
dc.identifier.otherWOS: 000632978700001
dc.identifier.otherScopus: 85105004638
dc.identifier.urihttps://hdl.handle.net/10023/21757
dc.descriptionWe gratefully acknowledge the University of Ferrara (Bando Giovani Ricercatori 2019) for financial support (AB). The Chinese Scholarship Scheme and University of St Andrews are thanked for a CSC Scholarship (S. Q.). Aix-Marseille University, CNRS, and ANR (Agence Nationale de la Recherche) (AMPLI project ANR-18-CE07-0036) are also gratefully acknowledged for funding (TD, XL and CB).en
dc.description.abstractThe sequential acylative kinetic resolution (KR) of C2-symmetric (±)-1,2-syn and (±)-1,3-anti-diols using a packed bed microreactor loaded with the polystyrene-supported isothiourea, HyperBTM, is demonstrated in flow. The sequential KRs of C2-symmetric (±)-1,2-syn and (±)-1,3-anti-diols exploits Horeau amplification, with each composed of two successive KR processes, with each substrate class significantly differing in the relative rate constants for each KR process. Optimisation of the continuous flow set-up for both C2-symmetric (±)-1,2-syn and (±)-1,3-anti-diol substrate classes allowed isolation of reaction products in both high enantiopurity and yield. In addition to the successful KR of C2-symmetric (±)-1,2-syn and (±)-1,3-anti-diols, the application of this process to the more conceptually-complex scenario involving the sequential KR of C1-symmetric (±)-1,3-anti-diols was demonstrated, which involve eight independent rate constants.
dc.format.extent8
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.rightsCopyright © 2021 The Author(s). Open Access. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.en
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleHoreau amplification in the sequential acylative kinetic resolution of (±)-1,2-diols and (±)-1,3-diols in flowen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doihttps://doi.org/10.1039/D1OB00304F
dc.description.statusPeer revieweden


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