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dc.contributor.authorBoyce, Gregory
dc.contributor.authorMusolino, Stefania F.
dc.contributor.authorYang, Jianing
dc.contributor.authorSmith, Andrew D.
dc.contributor.authorTaylor, James
dc.date.accessioned2022-09-09T08:30:26Z
dc.date.available2022-09-09T08:30:26Z
dc.date.issued2022-10-07
dc.identifier.citationBoyce , G , Musolino , S F , Yang , J , Smith , A D & Taylor , J 2022 , ' Arylboronic acid-catalyzed racemization of secondary and tertiary alcohols ' , The Journal of Organic Chemistry , vol. 87 , no. 19 , pp. 13367-13374 . https://doi.org/10.1021/acs.joc.2c01602en
dc.identifier.issn0022-3263
dc.identifier.otherPURE: 281039177
dc.identifier.otherPURE UUID: 9b2d632e-00eb-4279-a698-7be99ae36ec7
dc.identifier.otherORCID: /0000-0002-2104-7313/work/118800374
dc.identifier.otherWOS: 000859819900001
dc.identifier.otherScopus: 85137897701
dc.identifier.urihttp://hdl.handle.net/10023/25982
dc.descriptionFunding: Florida Gulf Coast University; University of St Andrews; UK Engineering and Physical Sciences Research Council - EP/J018139/1, EP/L016419/1, EP/V051423/1; Leverhulme Trust - ECF-2014-005.en
dc.description.abstractThe use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate.
dc.format.extent8
dc.language.isoeng
dc.relation.ispartofThe Journal of Organic Chemistryen
dc.rightsCopyright © 2022 The Authors. Published by American Chemical Society. Open Access. This article is distributed under the terms of the Creative Commons Attribution 4.0 License (https://creativecommons.org/licenses/by/4.0/) which permits any use, reproduction and distribution of the work without further permission provided the original work is attributeden
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleArylboronic acid-catalyzed racemization of secondary and tertiary alcoholsen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Leverhulme Trusten
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doihttps://doi.org/10.1021/acs.joc.2c01602
dc.description.statusPeer revieweden
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberEP/L016419/1en
dc.identifier.grantnumberECF-2014-005en


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