Asymmetric Reduction of Monoketo Hexadecanoic Acid Methyl Esters

TÜRKER G., Yusufoglu A. S.

ASIAN JOURNAL OF CHEMISTRY, vol.25, no.3, pp.1531-1535, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 25 Issue: 3
  • Publication Date: 2013
  • Journal Name: ASIAN JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1531-1535
  • Istanbul University Affiliated: Yes

Abstract

Methyl 2-,3-,6-,8-,14- and 15-keto hexadecanoates were reduced by using NaBH4 in presence of 1,2;5,6-di-O-isopropilydene-D-glucofuranose [DIPGH], R(+)-1,1'-binaphthyl-2,2'-diol [RBND] and pivalic acid [PA]. The reduction of 2- and 3-keto esters in the presence of (+)-1,1'-binaphthyl-2,2'-diol results in considerably higher stereoselectivities (95 % ee). Enantiometric excess (ee %) was determined by H-1 and C-13 NMR analyses using a shift reagent, Eu(tfc)(3).