A series of novel ?-hydroxyamide based catalysts for borane-mediated enantioselective reductions of prochiral ketones
dc.contributor.author | Azizoglu, Murat | |
dc.contributor.author | Erdogan, Asli | |
dc.contributor.author | Arslan, Nevin | |
dc.contributor.author | Turgut, Yilmaz | |
dc.contributor.author | Hosgoren, Halil | |
dc.contributor.author | Pirinccioglu, Necmettin | |
dc.date.accessioned | 2024-04-24T16:18:28Z | |
dc.date.available | 2024-04-24T16:18:28Z | |
dc.date.issued | 2016 | |
dc.department | Dicle Üniversitesi | en_US |
dc.description.abstract | The enantioselective reduction of prochiral ketones with borane in the presence of a chiral ligand has received considerable attention. Hydroxylamine-based chiral ligands with amide and hydroxyl functions in the presence of other co-ordinating groups are highly effective in these asymmetric reductions. The current work presents a simple one step synthesis of a series of beta-hydroxyamide-based ligands from the reaction between 3-hydroxy-2-naphthoic acid and chiral amino alcohols and their applications as catalysts in asymmetric borane-mediated reductions of aromatic prochiral ketones in THE The reductions provided the corresponding secondary alcohols with up to 96% ee and in good to excellent yields (89-99%). OFF calculations at B3LYP/6-31+g(d) level offered theoretical models to account for the enantioselectivity imposed by the chiral ligands in the reductions of the ketones. (C) 2016 Elsevier Ltd. All rights reserved. | en_US |
dc.description.sponsorship | Scientific and Technological Research Council of Turkey (TUBITAK) [110 T 809] | en_US |
dc.description.sponsorship | We would like to thank The Scientific and Technological Research Council of Turkey (TUBITAK) for financially supporting this research (Project No: 110 T 809). | en_US |
dc.identifier.doi | 10.1016/j.tetasy.2016.06.003 | |
dc.identifier.endpage | 622 | en_US |
dc.identifier.issn | 0957-4166 | |
dc.identifier.issue | 14-15 | en_US |
dc.identifier.scopus | 2-s2.0-84977098563 | |
dc.identifier.scopusquality | N/A | |
dc.identifier.startpage | 614 | en_US |
dc.identifier.uri | https://doi.org/10.1016/j.tetasy.2016.06.003 | |
dc.identifier.uri | https://hdl.handle.net/11468/16115 | |
dc.identifier.volume | 27 | en_US |
dc.identifier.wos | WOS:000380419800004 | |
dc.identifier.wosquality | Q2 | |
dc.indekslendigikaynak | Web of Science | |
dc.indekslendigikaynak | Scopus | |
dc.language.iso | en | en_US |
dc.publisher | Pergamon-Elsevier Science Ltd | en_US |
dc.relation.ispartof | Tetrahedron-Asymmetry | |
dc.relation.publicationcategory | Makale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı | en_US |
dc.rights | info:eu-repo/semantics/closedAccess | en_US |
dc.subject | [No Keyword] | en_US |
dc.title | A series of novel ?-hydroxyamide based catalysts for borane-mediated enantioselective reductions of prochiral ketones | en_US |
dc.title | A series of novel ?-hydroxyamide based catalysts for borane-mediated enantioselective reductions of prochiral ketones | |
dc.type | Article | en_US |