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dc.contributor.authorBitai, Jacqueline
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorCordes, David B.
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2020-05-28T09:30:04Z
dc.date.available2020-05-28T09:30:04Z
dc.date.issued2020-05-25
dc.identifier.citationBitai , J , Slawin , A M Z , Cordes , D B & Smith , A D 2020 , ' Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives ' , Molecules , vol. 25 , no. 10 , 2463 . https://doi.org/10.3390/molecules25102463en
dc.identifier.issn1420-3049
dc.identifier.otherPURE: 268098165
dc.identifier.otherPURE UUID: a40fb1f8-eaab-4964-9e75-75c8cb2e4c96
dc.identifier.otherORCID: /0000-0002-2104-7313/work/74872801
dc.identifier.otherORCID: /0000-0002-9527-6418/work/74872895
dc.identifier.otherORCID: /0000-0002-5366-9168/work/74872967
dc.identifier.otherScopus: 85085635491
dc.identifier.otherWOS: 000539293400196
dc.identifier.urihttp://hdl.handle.net/10023/20002
dc.descriptionFunding: This research was funded by the School of Chemistry, University of St Andrews. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractThe scope and limitations of a tandem N-allylation/[2,3]-rearrangementprotocol are investigated through the incorporation of a variety of functionalgroups within an allylic phosphate precursor. This method uses readilyaccessible N,N-dimethylglycine aryl esters and functionalizedallylic phosphates, forming quaternary ammonium salts in situ in the presence of a palladium catalyst. Subsequentenantioselective [2,3]-sigmatropic rearrangement, promoted by the chiralisothiourea tetramisole, generates α-amino acid derivatives with two contiguousstereocenters. The incorporation of electron withdrawing ester and amide groupsgave the best results, furnishing the desired products in moderate to goodyields (29-70%), with low diastereocontrol (typically 60:40 dr) but highenantioselectivity (up to 90:10 er). These results indicate that substrate-catalystinteractions in the proposed transition state are sensitive to the substitutionpattern of the substrates.
dc.format.extent13
dc.language.isoeng
dc.relation.ispartofMoleculesen
dc.rightsCopyright © 2020 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 (http://creativecommons.org/licenses/by/4.0/).en
dc.subjectIsothioureaen
dc.subjectPalladiumen
dc.subjectEnantioselective catalysisen
dc.subjectAmino acidsen
dc.subject[2,3]-rearrangementen
dc.subjectN-allylationen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleExploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivativesen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.3390/molecules25102463
dc.description.statusPeer revieweden


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