Asymmetric Meerwein-Ponndorf-Verley reduction of long chain keto alkanoic acid methyl esters


Onar H. C. , Hasdemir B. , Yusufoglu A. S.

JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, vol.72, no.5, pp.421-427, 2007 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 72 Issue: 5
  • Publication Date: 2007
  • Doi Number: 10.2298/jsc0705421o
  • Title of Journal : JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
  • Page Numbers: pp.421-427

Abstract

3-, 7- and 13-Monoketo tetradecanoic acid methyl esters carrying a keto group at the ends and at the middle of the chain with 14 carbon atoms were reduced by a Meerwein-Ponndorf-Verley reaction in the presence of R-(+)-1,1'-binaphthalcne-2,2'-diol, 1,2:5,6-D-di-O-isopropylidene-D-mannitol and L-(-)-menthol. The highest enantiomeric purity of 65% ee was found for 13-hydroxy ester isomer. The enantiomeric excess was determined by H-1-NMR shift with Eu(tfc)(3) and by optical rotation.