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Vol. 26 No. 2 (2014): Vol 26 Issue 2

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Enantioselective Hydrogenation of Ethyl Pyruvate Catalyzed by 1,2-Diphenyl-ethylenediamine-Modified Iridium Complex: Effect of Solvent

https://doi.org/10.14233/ajchem.2014.15372
You Du
Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China *Corresponding authors: Tel/Fax: +86 28 85412904; E-mail: scuhchen@163.com
Chun Li
Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China *Corresponding authors: Tel/Fax: +86 28 85412904; E-mail: scuhchen@163.com
Xiaoyun Tan
Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China *Corresponding authors: Tel/Fax: +86 28 85412904; E-mail: scuhchen@163.com
Haiyan Fu
Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China *Corresponding authors: Tel/Fax: +86 28 85412904; E-mail: scuhchen@163.com
Xueli Zheng*
Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China *Corresponding authors: Tel/Fax: +86 28 85412904; E-mail: scuhchen@163.com
Ruixiang Li
Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China *Corresponding authors: Tel/Fax: +86 28 85412904; E-mail: scuhchen@163.com
Hua Chen*
Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China *Corresponding authors: Tel/Fax: +86 28 85412904; E-mail: scuhchen@163.com

Asian Journal of Chemistry, Vol. 26 No. 2 (2014): Vol 26 Issue 2

Abstract

The enantioselective hydrogenation of ethyl pyruvate was explored by a readily available homogeneous iridium catalysis system. It was found that (1R,2R)-(+)-1,2-diphenyl-ethylenediamine [(1R,2R)-DPEN] modified [Ir(COD)Cl]2 (COD = cis,cis-1,5-cyclooctadiene) was highly active for the enantioselective hydrogenation of ethyl pyruvate, and the moderate enantioselectivity of 29 % was obtained (the best value reported by iridium catalysts was 39 %). NMR spectroscopy proved that hydrogen bond between the solvent and the a-carbonyl of ethyl pyruvate would be favor to the enantioselective hydrogenation.

Keywords

Enantioselective hydrogenation Iridium catalysts Solvent effect NMR Spectroscopy Hydrogen bond.
Du, Y., Li, C., Tan, X., Fu, H., Zheng*, X., Li, R., & Chen*, H. (2014). Enantioselective Hydrogenation of Ethyl Pyruvate Catalyzed by 1,2-Diphenyl-ethylenediamine-Modified Iridium Complex: Effect of Solvent. Asian Journal of Chemistry, 26(2), 319–322. https://doi.org/10.14233/ajchem.2014.15372
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