Asymmetric synthesis of monohydroxy tetradecanoic acids and their methyl esters

Hasdemir B., Yusufoglu A. S.

TETRAHEDRON-ASYMMETRY, vol.15, no.1, pp.65-68, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 1
  • Publication Date: 2004
  • Doi Number: 10.1016/j.tetasy.2003.10.020
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.65-68
  • Istanbul University Affiliated: Yes

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.