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Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine
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dc.contributor.author | Cormanich, Rodrigo A. | |
dc.contributor.author | Zeoly, Lucas A. | |
dc.contributor.author | Santos, Hugo | |
dc.contributor.author | Camilo, Nilton S. | |
dc.contributor.author | Bühl, Michael | |
dc.contributor.author | Coelho, Fernando | |
dc.date.accessioned | 2020-11-04T12:30:06Z | |
dc.date.available | 2020-11-04T12:30:06Z | |
dc.date.issued | 2020-09-04 | |
dc.identifier | 270821964 | |
dc.identifier | f2bbb589-c140-473b-ad13-3f1b3cf60bc0 | |
dc.identifier | 85092141771 | |
dc.identifier | 000569376800047 | |
dc.identifier.citation | Cormanich , 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 ' , The Journal of Organic Chemistry , vol. 85 , no. 17 , pp. 11541-11548 . https://doi.org/10.1021/acs.joc.0c01338 | en |
dc.identifier.issn | 0022-3263 | |
dc.identifier.other | RIS: urn:C402CF7F7E1CCEA9E0F19ED38365032A | |
dc.identifier.other | ORCID: /0000-0002-1095-7143/work/82500876 | |
dc.identifier.uri | https://hdl.handle.net/10023/20895 | |
dc.description | The 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.abstract | In 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.extent | 8 | |
dc.format.extent | 1405655 | |
dc.language.iso | eng | |
dc.relation.ispartof | The Journal of Organic Chemistry | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Origin of the diastereoselectivity of the heterogeneous hydrogenation of a substituted indolizine | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1021/acs.joc.0c01338 | |
dc.description.status | Peer reviewed | en |
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