Diastereoselective addition of alkenylchromium(III) reagents to Garner’s aldehyde: Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides | Zendy

Zorana Ferjančić | Zendy; Radomir Matović | Zendy; Filip Bihelović | Zendy

Open Access

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

Author(s) -

Zorana Ferjančić,

Radomir Matović,

Filip Bihelović

Publication year - 2013

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc130611067f

Subject(s) - aldehyde , stereoselectivity , chemistry , reagent , allylic rearrangement , stereochemistry , coupling reaction , combinatorial chemistry , organic chemistry , catalysis

The intermolecular Nozaki-Hiyama-Kishi coupling between alkenylchromium(III) reagents, derived from either (E)-2-bromostyrene or (E)-1-iodopentadec-1-ene, and conformationally rigid Garner's aldehyde resulted in stereoselective formation of Felkin-type allylic alcohols in good yields, thus providing an easy access to sphingosines. In addition, when the protecting group in Garner's aldehyde was changed (from Boc to N-octanoyl), a reversal of stereoselectivity was observed in the reaction with (E)-pentadec-1-enylchromium(III), probably as a result of hydrophobic interactions between long carbon chains of the reaction partners. [Projekat Ministarstva nauke Republike Srbije, br. 172027

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