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Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides

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2014
1555.pdf (323.3Kb)
Autori
Ferjančić, Zorana
Matović, Radomir
Bihelović, Filip
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentu
Apstrakt
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.
Ključne reči:
Nozaki-Hiyama-Kishi reaction / sphingosine / Garner's aldehyde / organochromium reagent
Izvor:
Journal of the Serbian Chemical Society, 2014, 79, 6, 627-636
Izdavač:
  • Serbian Chemical Soc, Belgrade
Projekti:
  • Razvoj novih sintetičkih metoda i njihova primena u sintezi prirodnih proizvoda i biološki aktivnih jedinjenja (RS-172027)

DOI: 10.2298/JSC130611067F

ISSN: 0352-5139

WoS: 000338268800001

Scopus: 2-s2.0-84903158162
[ Google Scholar ]
2
2
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1557
Kolekcije
  • Radovi istraživača / Researchers' publications
Institucija
IHTM
TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Bihelović, Filip
PY  - 2014
UR  - http://cer.ihtm.bg.ac.rs/handle/123456789/1557
AB  - 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.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides
VL  - 79
IS  - 6
SP  - 627
EP  - 636
DO  - 10.2298/JSC130611067F
ER  - 
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Bihelović, Filip",
year = "2014",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/1557",
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.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides",
volume = "79",
number = "6",
pages = "627-636",
doi = "10.2298/JSC130611067F"
}
Ferjančić Z, Matović R, Bihelović F. Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides. Journal of the Serbian Chemical Society. 2014;79(6):627-636
Ferjančić, Z., Matović, R.,& Bihelović, F. (2014). Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides.
Journal of the Serbian Chemical SocietySerbian Chemical Soc, Belgrade., 79(6), 627-636.
https://doi.org/10.2298/JSC130611067F
Ferjančić Zorana, Matović Radomir, Bihelović Filip, "Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides" 79, no. 6 (2014):627-636,
https://doi.org/10.2298/JSC130611067F .

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