Asymmetric synthesis of monohydroxy tetradecanoic acids and their methyl esters

Abstract

Methyl 3-, 6- and 13-oxo tetradecanoates were reduced by NaBH4 in the presence of 1,2:5,6-di-O-isopropylidene-Dglucofuranose (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 H-1 NNIR with shift reagent, EU(tfc)(3). (C) 2003 Elsevier Ltd. All rights reserved.