Asymmetric synthesis of monohydroxy tetradecanoic acids and their methyl esters

Graphic Methyl 3-, 6- and 13-oxo tetradecanoates were reduced by NaBH 4 in the presence of 1,2:5,6-di- O-isopropylidene- d-glucofuranose (DIPGH) and (−)-menthol together with isovaleric and pivalic acids in THF solution. The highest enantiomeric purity was found for the 13-hydroxy ester isomer of 96...

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Published in:Tetrahedron: asymmetry 2004-01, Vol.15 (1), p.65-68
Main Authors: Hasdemir, Belma, Yusufoğlu, Ayşe
Format: Article
Language:English
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Summary:Graphic Methyl 3-, 6- and 13-oxo tetradecanoates were reduced by NaBH 4 in the presence of 1,2:5,6-di- O-isopropylidene- d-glucofuranose (DIPGH) and (−)-menthol together with isovaleric and pivalic acids in THF solution. The highest enantiomeric purity was found for the 13-hydroxy ester isomer of 96% ee. Enantiomeric excess (ee, %) was determined by chiral HPLC and 1H NMR with shift reagent, Eu(tfc) 3.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2003.10.020