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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 05: 900 - 906

DOI: https://doi.org/DOI:10.6023/cjoc1201061

Articles

Synthesis of Rosin Derived Chiral derivatizing agents for 31P NMR assays of amine or alcohol and amino alcohol enantiomers

  • Wu Qiang ,
  • Yao Guiyang ,
  • Zhu Yongtao ,
  • Wang Hengshan ,
  • He Chunhuan ,
  • Pan Yingming
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  • Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004

Received date: 2012-01-06

  Revised date: 2012-03-01

  Online published: 2012-03-23

Supported by

Project supported by the National Natural Science Foundation of China (No. 20762001), the Natural Science Foundation of Guangxi Province (No. 2011GXNSFD018010) and the Project of Ten, Hundred, Thousand Distinguished Talents in New Century of Guangxi Province (No. 2007228).

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Abstract

Chiral alcohols (3, 6) were synthesized in optically pure forms from easily available rosin acid in short-steps. A comprehensive protocol for the enantiomeric excess assays of mono or di functional-grouped chiral secondary amine or alcohol has been established by using them as chiral auxiliary for chiral phosphorus derivatizing reagents (CPDA) in 31P NMR tests. Chemical shift difference (Δδp) values ranging from 3.08 to 0.10 ppm between two diastereoisomers of the CPDAs and the aryl substrates was obtained. The enantiomeric excess of 1-(1-Naphthyl)ethylamine and 1,1’-Bi(2-naphthol) were determined using our (CPDA), the results showed that the relative error was less than ±2%.

Key words： 31P NMR; enantiomeric excess detection; rosin derived phosphine agents

Cite this article

Wu Qiang , Yao Guiyang , Zhu Yongtao , Wang Hengshan , He Chunhuan , Pan Yingming . Synthesis of Rosin Derived Chiral derivatizing agents for 31P NMR assays of amine or alcohol and amino alcohol enantiomers[J]. Chinese Journal of Organic Chemistry, 2012 , 32(05) : 900 -906 . DOI: DOI:10.6023/cjoc1201061

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