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Further studies on the [1,2]-Wittig rearrangement of 2-(2-benzyloxy)aryloxazolines

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dc.contributor.authorAitken, R Alan
dc.contributor.authorHarper, Andrew D.
dc.contributor.authorInwood, Ryan
dc.date.accessioned2022-05-17T11:30:13Z
dc.date.available2022-05-17T11:30:13Z
dc.date.issued2022-05-17
dc.identifier.citationAitken , R A , Harper , A D & Inwood , R 2022 , ' Further studies on the [1,2]-Wittig rearrangement of 2-(2-benzyloxy)aryloxazolines ' , Molecules , vol. 27 , no. 10 , 3186 . https://doi.org/10.3390/molecules27103186en
dc.identifier.issn1420-3049
dc.identifier.otherPURE: 279577509
dc.identifier.otherPURE UUID: 1dffc0b9-6934-47fd-922e-c9de49c3f9c8
dc.identifier.otherORCID: /0000-0001-6959-5311/work/113398829
dc.identifier.otherScopus: 85130828896
dc.identifier.otherWOS: 000803401000001
dc.identifier.urihttps://hdl.handle.net/10023/25389
dc.descriptionAuthors thank EPSRC (UK) for a DTA studentship to ADH (Grant EP/L505079/1), EPSRC (UK) and CRITICAT Centre for Doctoral Training for a studentship to R. A. I. (Grant code: EP/L016419/1) and the EPSRC UK National Mass Spectrometry Facility at Swansea University.en
dc.description.abstractThe behaviour of 14 ortho-functionalised 2-aryloxazolines, 11 of them prepared and characterised for the first time, with butyllithium has been examined. Significant limitations to the Wittig rearrangement of such systems are revealed. In terms of asymmetric Wittig rearrangement, good diastereoselectivity is obtained with a valine-derived 4-isopropyl oxazoline but this is compromised by racemisation upon hydrolysis. More encouraging selectivity is achieved in the Wittig rearrangement of an acyclic phenylalanine-derived ortho-benzyloxy benzamide.
dc.format.extent23
dc.language.isoeng
dc.relation.ispartofMoleculesen
dc.rightsCopyright © 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).en
dc.subjectOxazolineen
dc.subjectWittig rearrangementen
dc.subjectPhthalideen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleFurther studies on the [1,2]-Wittig rearrangement of 2-(2-benzyloxy)aryloxazolinesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doihttps://doi.org/10.3390/molecules27103186
dc.description.statusPeer revieweden
dc.identifier.grantnumberEP/L016419/1en


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