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dc.contributor.authorCormanich, Rodrigo A.
dc.contributor.authorZeoly, Lucas A.
dc.contributor.authorSantos, Hugo
dc.contributor.authorCamilo, Nilton S.
dc.contributor.authorBühl, Michael
dc.contributor.authorCoelho, Fernando
dc.date.accessioned2020-11-04T12:30:06Z
dc.date.available2020-11-04T12:30:06Z
dc.date.issued2020-09-04
dc.identifier.citationCormanich , R A , Zeoly , L A , Santos , H , Camilo , N S , Bühl , M & Coelho , F 2020 , ' Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine ' , Journal of Organic Chemistry , vol. 85 , no. 17 , pp. 11541-11548 . https://doi.org/10.1021/acs.joc.0c01338en
dc.identifier.issn0022-3263
dc.identifier.otherPURE: 270821964
dc.identifier.otherPURE UUID: f2bbb589-c140-473b-ad13-3f1b3cf60bc0
dc.identifier.otherRIS: urn:C402CF7F7E1CCEA9E0F19ED38365032A
dc.identifier.otherScopus: 85092141771
dc.identifier.otherORCID: /0000-0002-1095-7143/work/82500876
dc.identifier.otherWOS: 000569376800047
dc.identifier.urihttp://hdl.handle.net/10023/20895
dc.descriptionThe authors are grateful to FAPESP for the financial support of this research. The authors also thank FAPESP for the fellowships to R.A.C. (#2018/03910-1) and F.C. (#2013/07600-3 and #2018/02611-3) and for a scholarship to H.S. (#2015/09205-0) and CNPq for a scholarship to L.A.Z. and a research fellowship for F.C, (307840/2014-0, 422890/2016-2 and 301330/2016-2). L.A.Z. also thanks Capes for a scholarship.en
dc.description.abstractIn this work, the stereoselective heterogeneous hydrogenation of a tetrasubstituted indolizine was studied. Partial hydrogenation products were obtained in three steps from a substituted pyridine-2-carboxaldehyde prepared from commercial pyridoxine hydrochloride. The hydrogenation of the indolizine ring was shown to be diastereoselective, forming trans-6b and cis-9. Theoretical calculations (ab initio and DFT) were used to rationalize the unusual trans stereoselectivity for 6b, and a keto–enol tautomerism under kinetic control has been proposed as the source of diastereoselectivity.
dc.format.extent8
dc.language.isoeng
dc.relation.ispartofJournal of Organic Chemistryen
dc.rightsCopyright © 2020 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.en
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleOrigin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizineen
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/10.1021/acs.joc.0c01338
dc.description.statusPeer revieweden


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