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On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes
dc.creator | Marjanović-Trajković, Jasna | |
dc.creator | Milanović, Vesna D. | |
dc.creator | Ferjančić, Zorana | |
dc.creator | Saičić, Radomir | |
dc.date.accessioned | 2018-11-22T00:39:20Z | |
dc.date.available | 2018-11-22T00:39:20Z | |
dc.date.issued | 2017 | |
dc.identifier.issn | 1434-193X | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/2410 | |
dc.description.abstract | Reagent stereocontrol in the proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxane-5-one 1 with chiral aldehydes has been investigated. Synthetically useful levels of diastereoselectivity could be achieved in reactions with acyclic chiral alpha-oxy and alpha-amino aldehydes in both matched and mismatched cases. By using this reaction as a key step, two medicinally relevant azasugars, 1-deoxy-galactonojirimycin (9) and 2,5-dideoxy-2,5-imino-d-altritol (10), were efficiently synthesized. | en |
dc.publisher | Wiley-V C H Verlag Gmbh, Weinheim | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172027/RS// | |
dc.relation | Serbian Academy of Sciences and Arts [F193] | |
dc.rights | restrictedAccess | |
dc.source | European Journal of Organic Chemistry | |
dc.subject | Synthetic methods | en |
dc.subject | Organocatalysis | en |
dc.subject | Aldol reactions | en |
dc.subject | Iminosugars | en |
dc.subject | Diastereoselectivity | en |
dc.title | On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Милановић, Весна; Ферјанчић, Зорана; Саичић, Радомир; Марјановић-Трајковић, Јасна; | |
dc.citation.issue | 41 | |
dc.citation.spage | 6146 | |
dc.citation.epage | 6153 | |
dc.identifier.wos | 000414849900007 | |
dc.identifier.doi | 10.1002/ejoc.201701073 | |
dc.citation.other | (41): 6146-6153 | |
dc.citation.rank | M22 | |
dc.description.other | Supplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3229] | |
dc.type.version | publishedVersion | en |
dc.identifier.scopus | 2-s2.0-85033474381 |