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Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions
dc.creator | Stojanović, Milovan | |
dc.creator | Marković, Rade | |
dc.creator | Kleinpeter, Erich | |
dc.creator | Baranac-Stojanović, Marija | |
dc.date.accessioned | 2019-01-30T17:30:32Z | |
dc.date.available | 2019-01-30T17:30:32Z | |
dc.date.issued | 2012 | |
dc.identifier.issn | 1477-0520 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/1011 | |
dc.description.abstract | Syntheses of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined and discussed. The formation of (5,6)-membered systems was feasible with all nucleophiles tried (O, S and N), while the closing of the five-membered ring was restricted to O- and S-nucleophiles. The closure of a four-membered ring failed. Instead, the bicyclic (5,6)-membered acetal derivative and the tricyclic system with an eight-membered central ring were obtained from the substrates containing O and S nucleophilic moieties, respectively. The reaction outcome and stereochemistry are rationalized using quantum chemical calculations at B3LYP/6-31G(d) level. The exclusive cis-stereoselectivity in the formation of (5,6)- and (5,5)-membered systems results from thermodynamic control, whereas the formation of the eight-membered ring was kinetically controlled. | en |
dc.publisher | Royal Soc Chemistry, Cambridge | |
dc.relation | info:eu-repo/grantAgreement/MESTD/MPN2006-2010/142007/RS// | |
dc.relation | Deutscher Akademischer Austauschdienst (DAAD) [504 252 70] | |
dc.rights | restrictedAccess | |
dc.source | Organic & Biomolecular Chemistry | |
dc.title | Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Стојановић, Милован; Марковиц, Раде; Баранац-Стојановиц, Марија; Клеинпетер, Ерицх; | |
dc.citation.volume | 10 | |
dc.citation.issue | 3 | |
dc.citation.spage | 575 | |
dc.citation.epage | 589 | |
dc.citation.other | 10(3): 575-589 | |
dc.citation.rank | M21 | |
dc.identifier.pmid | 22113469 | |
dc.identifier.doi | 10.1039/c1ob06451g | |
dc.identifier.scopus | 2-s2.0-84055214179 | |
dc.identifier.wos | 000298750800018 | |
dc.type.version | publishedVersion |