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In situ synthesis of rosin derived chiral derivatizing agents for 31P NMR assays of amine and alcohol enantiomers

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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 di-functional-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(Δδ P) values ranging from 4.5 to 0.15 between two diastereoisomers of the CPDAs and the aryl substrates were obtained. Positive Δδ R-S was observed for all the tested alcohol P(III) and P(V) derivatives, while negative Δδ R-S was observed for all the amines.

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References

  1. Błażewska K. M., Gajda T., Tetrahedron: Asymmetry, 2009, 20, 1337

    Article  Google Scholar 

  2. Amberg M., Kempter I., Bergsträßer U., Stapf G., Hartung J., Tetrahedron: Asymmetry, 2011, 22, 752

    Article  CAS  Google Scholar 

  3. Wenzel T. J., Chisholm C. D., Prog. Nucl. Magn. Reson. Spectrosc., 2011, 59, 1

    Article  CAS  Google Scholar 

  4. Wenzel T. J., Wilcox J. D., Chirality, 2003, 15, 256

    Article  CAS  Google Scholar 

  5. Wang Z., Li Z. Q., Yu D. H., Weng L., Liu M., Zhang G. R., Cao S. G., Chem. Res. Chinese Universities, 2004, 20(5), 575

    CAS  Google Scholar 

  6. Wenzel T. J., Thurston J. E., J. Org. Chem., 2000, 65, 5

    Article  Google Scholar 

  7. Lovely A. E., Wenzel T. J., Org. Lett., 2006, 8, 2823

    Article  CAS  Google Scholar 

  8. Joseph G., Chirality, 2008, 20, 5

    Article  Google Scholar 

  9. Thomas R., Frederik N., Naraschewski J. E., Tetrahedron: Asymmetry, 2009, 20, 362

    Article  Google Scholar 

  10. Finn M. G., Chirality, 2002, 14, 534

    Article  CAS  Google Scholar 

  11. Zhu L., Shabbir S. H., Anslyn E. V., Chem. Eur. J., 2006, 13, 99

    Article  Google Scholar 

  12. Mirri G., Bull S. D., Horton P. N., James T. D., Male L., Tucker J. H. R., J. Am. Chem. Soc., 2010, 132, 8903

    Article  CAS  Google Scholar 

  13. Demchuk O. M., Świerczynska W., Pietrusiewicz K. M., Woźnica M., Wójcik D., Frelek J., Tetrahedron: Asymmetry, 2008, 19, 2339

    Article  CAS  Google Scholar 

  14. Chauvin A. S., Bernardinelli G., Alexakis A., Tetrahedron: Asymmetry, 2006, 17, 2203

    Article  CAS  Google Scholar 

  15. Chi Y. G., Peelen T. J., Gellman S. H., Org. Lett., 2005, 7, 3469

    Article  CAS  Google Scholar 

  16. Wu Q., Yao G. Y., Zhu Y. T., Wang H. S., He C. H., Pan Y. M., Chin. J. Org. Chem., 2011, 32, 900

    Article  Google Scholar 

  17. Seebacher W., Hüfner A., Haslinger E., Weis R., Monatsh. Chem., 1998, 129, 697

    CAS  Google Scholar 

  18. Khlebnikova T. B., Karpyshev N. N., Tolstilova O. V., Tolstilova A. G., Chirality, 2004, 16, S40

    Article  CAS  Google Scholar 

  19. Benniston A. C., Gunning P., Peacock R. D., J. Org. Chem., 2005, 70, 115

    Article  CAS  Google Scholar 

  20. Yang G. S., Yan B., Lei L., Wang W. G., Liu C. B., Chem. J. Chinese Universities, 2000, 21(11), 1745

    CAS  Google Scholar 

  21. Rekharsky M., Inoue Y., J. Am. Chem. Soc., 2000, 122, 4418

    Article  CAS  Google Scholar 

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Authors and Affiliations

  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

    Qiang Wu, Gui-yang Yao, Ye Zhang, Heng-shan Wang, Lin Yang, Yong-tao Zhu & Ying-ming Pan

Authors
  1. Qiang Wu
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  2. Gui-yang Yao
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  3. Ye Zhang
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  4. Heng-shan Wang
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  5. Lin Yang
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  6. Yong-tao Zhu
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  7. Ying-ming Pan
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Corresponding authors

Correspondence to Heng-shan Wang or Ying-ming Pan.

Additional information

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

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Wu, Q., Yao, Gy., Zhang, Y. et al. In situ synthesis of rosin derived chiral derivatizing agents for 31P NMR assays of amine and alcohol enantiomers. Chem. Res. Chin. Univ. 29, 894–899 (2013). https://doi.org/10.1007/s40242-013-3009-7

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  • DOI: https://doi.org/10.1007/s40242-013-3009-7

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