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dc.contributor.authorD'Hollander, Agathe C. A.
dc.contributor.authorWestwood, Nicholas J.
dc.date.accessioned2018-11-16T00:48:18Z
dc.date.available2018-11-16T00:48:18Z
dc.date.issued2018-01-11
dc.identifier.citationD'Hollander , A C A & Westwood , N J 2018 , ' Assessment of the regioselectivity in the condensation reaction of unsymmetrical o -phthaldialdehydes with alanine ' , Tetrahedron , vol. 74 , no. 2 , pp. 224-239 . https://doi.org/10.1016/j.tet.2017.11.035en
dc.identifier.issn0040-4020
dc.identifier.otherPURE: 251552506
dc.identifier.otherPURE UUID: cd797763-f047-4ac0-8c97-1abb4c36ccc4
dc.identifier.otherRIS: urn:1BE25EBD8F659F32AB9608F653F476B6
dc.identifier.otherScopus: 85036500463
dc.identifier.otherORCID: /0000-0003-0630-0138/work/56424145
dc.identifier.otherWOS: 000423248700002
dc.identifier.urihttp://hdl.handle.net/10023/16480
dc.descriptionFunding: We would like to thank the EPSRC DTG at the University of St Andrews for funding.en
dc.description.abstractOne approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding.
dc.language.isoeng
dc.relation.ispartofTetrahedronen
dc.rights© 2017 Elsevier Ltd. This work has been 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/10.1016/j.tet.2017.11.035en
dc.subjecto-phthaldialdehydeen
dc.subjectCondensation reactionen
dc.subjectRegioselectivityen
dc.subjectMechanistic understandingen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleAssessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanineen
dc.typeJournal articleen
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/10.1016/j.tet.2017.11.035
dc.description.statusPeer revieweden
dc.date.embargoedUntil2018-11-16
dc.identifier.urlhttp://www.sciencedirect.com/science/article/pii/S0040402017311833#appd001en


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