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Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (05): 900-906.DOI: DOI:10.6023/cjoc1201061 Previous Articles     Next Articles

Articles

用于芳香胺和醇NMR 对映体检测的松香基膦试剂的合成

吴强, 姚贵阳, 朱永涛, 王恒山, 何春欢, 潘英明   

  1. 广西师范大学化学化工学院 药用资源化学与药物分子工程重点实验室 桂林 541004
  • 收稿日期:2012-01-06 修回日期:2012-03-01 发布日期:2012-03-23
  • 通讯作者: 王恒山, 潘英明 E-mail:wang_hengshan@yahoo.com.cn
  • 基金资助:

    973 计划前期研究专项(No. 2011CB512005)、国家自然科学基金(No. 20762001)、广西自然科学基金重点(No. 2011GXNSFD018010)、广西新世纪十百千人才工程人选(No. 2007228)资助项目.

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   

  1. Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004
  • Received:2012-01-06 Revised:2012-03-01 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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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