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高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (5): 894-899.doi: 10.1007/s40242-013-3009-7

• Articles • 上一篇    下一篇

In situ Synthesis of Rosin Derived Chiral Derivatizing Agents for 31P NMR Assays of Amine and Alcohol Enantiomers

WU Qiang, YAO Gui-yang, ZHANG Ye, WANG Heng-shan, YANG Lin, ZHU Yong-tao, PAN Ying-ming   

  1. Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, P. R. China
  • 收稿日期:2013-01-07 修回日期:2013-03-11 出版日期:2013-10-01 发布日期:2013-09-17
  • 通讯作者: PAN Ying-ming, WANG Heng-shan E-mail:panym2005@sina.com;whengshan@163.com
  • 基金资助:

    Supported by the National Basic Research Program of China(No.2011CB512005), the National Natural Science Foundation of China(Nos.81260472 and 21101035), Guangxi Natural Science Foundation of China(Nos.2011GXNSFD018010 and 2010GXNSFF013001), the Project of Ten, Hundred, Thousand Distinguished Talents in New Century of Guangxi, China (No.2007228) and the State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China (No.CMEMR2012-A14).

In situ Synthesis of Rosin Derived Chiral Derivatizing Agents for 31P NMR Assays of Amine and Alcohol Enantiomers

WU Qiang, YAO Gui-yang, ZHANG Ye, WANG Heng-shan, YANG Lin, ZHU Yong-tao, PAN Ying-ming   

  1. Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, P. R. China
  • Received:2013-01-07 Revised:2013-03-11 Online:2013-10-01 Published:2013-09-17
  • Contact: PAN Ying-ming, WANG Heng-shan E-mail:panym2005@sina.com;whengshan@163.com
  • Supported by:

    Supported by the National Basic Research Program of China(No.2011CB512005), the National Natural Science Foundation of China(Nos.81260472 and 21101035), Guangxi Natural Science Foundation of China(Nos.2011GXNSFD018010 and 2010GXNSFF013001), the Project of Ten, Hundred, Thousand Distinguished Talents in New Century of Guangxi, China (No.2007228) and the State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China (No.CMEMR2012-A14).

摘要：

Chiral alcohols(3, 5) 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 difunctional-grouped chiral secondary amine or alcohol has been established with them used as chiral auxiliary for chiral phosphorus derivatizing agents(CPDAs) in 31P NMR tests. Chemical shift difference(ΔδP) values ranging from 4.5 to 0.15 between two diastereoisomers of the CPDAs and the aryl substrates were obtained. Positive ΔδR-S was observed for all the tested alcohol P(III) and P(V) derivatives, while negative ΔδR-S was observed for all the amines.

关键词: Chiral phosphorus derivatizing agent, Rosin, Enantiodiscrimination, 31P NMR

Abstract:

Chiral alcohols(3, 5) 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 difunctional-grouped chiral secondary amine or alcohol has been established with them used as chiral auxiliary for chiral phosphorus derivatizing agents(CPDAs) in 31P NMR tests. Chemical shift difference(ΔδP) values ranging from 4.5 to 0.15 between two diastereoisomers of the CPDAs and the aryl substrates were obtained. Positive ΔδR-S was observed for all the tested alcohol P(III) and P(V) derivatives, while negative ΔδR-S was observed for all the amines.

Key words: Chiral phosphorus derivatizing agent, Rosin, Enantiodiscrimination, 31P NMR