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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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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
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
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1557
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