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Vol. 25 No. 3 (2013): Vol 25 Issue 3

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Asymmetric Reduction of Monoketo Hexadecanoic Acid Methyl Esters

https://doi.org/10.14233/ajchem.2013.13126
Gülen Türker
Science and Technology Application and Research Center, Çanakkale Onsekiz Mart University, 17100 Çanakkale, Turkey
Ayse Yusufoglu
Department of Chemistry, Faculty of Engineering, Istanbul University, 34320 Avcilar, Istanbul, Turkey

Corresponding Author(s) : Gülen Türker

gturker@comu.edu.tr

Asian Journal of Chemistry, Vol. 25 No. 3 (2013): Vol 25 Issue 3

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 1H and 13C NMR analyses using a shift reagent, Eu(tfc)3.

Keywords

Reduction Enantiometric excess Keto hexadecanoates
Türker, G. ., & Yusufoglu, A. (2012). Asymmetric Reduction of Monoketo Hexadecanoic Acid Methyl Esters. Asian Journal of Chemistry, 25(3), 1531–1535. https://doi.org/10.14233/ajchem.2013.13126
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