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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

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