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dc.creatorFerjančić, Zorana
dc.creatorMatović, Radomir
dc.creatorBihelović, Filip
dc.date.accessioned2018-11-22T00:28:19Z
dc.date.available2018-11-22T00:28:19Z
dc.date.issued2014
dc.identifier.issn0352-5139
dc.identifier.urihttp://cherry.chem.bg.ac.rs/handle/123456789/1799
dc.description.abstractIntermolecular Nozaki-Hiyama-Kishi coupling between alkenylchromium(III) reagents, derived from either (E)-(2-bromoethenyl)benzene or (E)-1-iodo-1-pentadecene, and the conformationally rigid Garner's aldehyde resulted in the stereoselective formation of Felkin-type allylic alcohols in good yields, thus providing an easy access to sphingosines. In addition, when the protecting group in the Garner's aldehyde was changed (from Boc to N-octanoyl), a reversal of stereoselectivity was observed in the reaction with (E)-1-pentadecenylchromium(III), probably as the result of hydrophobic interactions between the long carbon chains of the reaction partners.en
dc.publisherSerbian Chemical Soc, Belgrade
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172027/RS//
dc.rightsopenAccess
dc.sourceJournal of the Serbian Chemical Society
dc.subjectNozaki-Hiyama-Kishi reactionen
dc.subjectsphingosineen
dc.subjectGarner's aldehydeen
dc.subjectorganochromium reagenten
dc.titleDiastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramidesen
dc.typearticle
dc.rights.licenseBY-NC-ND
dcterms.abstractБихеловић, Филип; Матовиц, Радомир; Ферјанчић, Зорана;
dc.citation.volume79
dc.citation.issue6
dc.citation.spage627
dc.citation.epage636
dc.identifier.wos000338268800001
dc.identifier.doi10.2298/JSC130611067F
dc.citation.other79(6): 627-636
dc.citation.rankM23
dc.type.versionpublishedVersion
dc.identifier.scopus2-s2.0-84903158162
dc.identifier.fulltexthttp://cherry.chem.bg.ac.rs/bitstream/id/8860/1797.pdf
dc.identifier.rcubKon_2682


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