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
Projects:
DOI: 10.2298/JSC130611067F
ISSN: 0352-5139