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dc.creatorStojanović, Milovan
dc.creatorMarkovic, Rade
dc.creatorKleinpeter, Erich
dc.creatorBaranac-Stojanović, Marija
dc.date.accessioned2019-01-30T17:30:32Z
dc.date.available2019-01-30T17:30:32Z
dc.date.issued2012
dc.identifier.issn1477-0520
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/1011
dc.description.abstractSyntheses 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.publisherRoyal Soc Chemistry, Cambridge
dc.relationinfo:eu-repo/grantAgreement/MESTD/MPN2006-2010/142007/RS//
dc.relationDeutscher Akademischer Austauschdienst (DAAD) [504 252 70]
dc.rightsrestrictedAccess
dc.sourceOrganic & Biomolecular Chemistry
dc.titleSynthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ionsen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractСтојановић, Милован; Марковиц, Раде; Баранац-Стојановиц, Марија; Клеинпетер, Ерицх;
dc.citation.volume10
dc.citation.issue3
dc.citation.spage575
dc.citation.epage589
dc.citation.other10(3): 575-589
dc.citation.rankM21
dc.identifier.pmid22113469
dc.identifier.doi10.1039/c1ob06451g
dc.identifier.rcubConv_2722
dc.identifier.scopus2-s2.0-84055214179
dc.identifier.wos000298750800018
dc.type.versionpublishedVersion


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