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, cilt.72, sa.5, ss.421-427, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 72 Sayı: 5
  • Basım Tarihi: 2007
  • Doi Numarası: 10.2298/jsc0705421o
  • Dergi Adı: JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.421-427
  • İstanbul Üniversitesi Adresli: Evet

Özet

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.