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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)
Authors
Ferjančić, Zorana
Matović, Radomir
Bihelović, Filip
Article (Published version)
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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.
Keywords:
Nozaki-Hiyama-Kishi reaction / sphingosine / Garner's aldehyde / organochromium reagent
Source:
Journal of the Serbian Chemical Society, 2014, 79, 6, 627-636
Publisher:
  • Serbian Chemical Soc, Belgrade
Funding / projects:
  • The development of new synthetic methods and their application in the synthesis of natural products and biologically active molecules (RS-172027)

DOI: 10.2298/JSC130611067F

ISSN: 0352-5139

WoS: 000338268800001

Scopus: 2-s2.0-84903158162
[ Google Scholar ]
2
2
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1557
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Bihelović, Filip
PY  - 2014
UR  - https://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",
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.. (2014). Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 79(6), 627-636.
https://doi.org/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. in Journal of the Serbian Chemical Society. 2014;79(6):627-636.
doi: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" in Journal of the Serbian Chemical Society, 79, no. 6 (2014):627-636,
https://doi.org/10.2298/JSC130611067F . .

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