dc.creator | Ferjančić, Zorana | |
dc.creator | Matović, Radomir | |
dc.creator | Bihelović, Filip | |
dc.date.accessioned | 2018-11-22T00:28:19Z | |
dc.date.available | 2018-11-22T00:28:19Z | |
dc.date.issued | 2014 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/1799 | |
dc.description.abstract | Intermolecular 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.publisher | Serbian Chemical Soc, Belgrade | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172027/RS// | |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Journal of the Serbian Chemical Society | |
dc.subject | Nozaki-Hiyama-Kishi reaction | en |
dc.subject | sphingosine | en |
dc.subject | Garner's aldehyde | en |
dc.subject | organochromium reagent | en |
dc.title | Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides | en |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dcterms.abstract | Бихеловић, Филип; Матовиц, Радомир; Ферјанчић, Зорана; | |
dc.citation.volume | 79 | |
dc.citation.issue | 6 | |
dc.citation.spage | 627 | |
dc.citation.epage | 636 | |
dc.identifier.wos | 000338268800001 | |
dc.identifier.doi | 10.2298/JSC130611067F | |
dc.citation.other | 79(6): 627-636 | |
dc.citation.rank | M23 | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-84903158162 | |
dc.identifier.fulltext | https://cherry.chem.bg.ac.rs/bitstream/id/8860/1797.pdf | |