Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides
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 reagentSource:
Journal of the Serbian Chemical Society, 2014, 79, 6, 627-636Publisher:
- Serbian Chemical Soc, Belgrade
Funding / projects:
DOI: 10.2298/JSC130611067F
ISSN: 0352-5139
WoS: 000338268800001
Scopus: 2-s2.0-84903158162
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IHTMTY - 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 . .