期刊文献+

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

In situ Synthesis of Rosin Derived Chiral Derivatizing Agents for 31p NMR Assays of Amine and Alcohol Enantiomers
原文传递
导出
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 di-functional-grouped chiral secondary amine or alcohol has been established with them used as chiral auxiliary for chiral phosphorus derivatizing agents(CPDAs) in 3Jp NMR tests. Chemical shift difference(△δp) values ranging from 4.5 to 0.15 between two dias- tereoisomers of the CPDAs and the aryl substrates were obtained. Positive △δR-S was observed for all the tested alco- hol P(III) and P(V) derivatives, while negative △δR-S was observed for all the amines. 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 3Jp NMR tests. Chemical shift difference(△δp) values ranging from 4.5 to 0.15 between two dias- tereoisomers of the CPDAs and the aryl substrates were obtained. Positive △δR-S was observed for all the tested alco- hol P(III) and P(V) derivatives, while negative △δR-S was observed for all the amines.
出处 《Chemical Research in Chinese Universities》 SCIE CAS CSCD 2013年第5期894-899,共6页 高等学校化学研究(英文版)
基金 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).
关键词 Chiral phosphorus derivatizing agent ROSIN ENANTIODISCRIMINATION 31p NMR Chiral phosphorus derivatizing agent Rosin Enantiodiscrimination 31p NMR
  • 相关文献

参考文献21

  • 1Btazewska K. M., Gajda T., Tetrahedron: Asymmetry, 2009, 20, 1337.
  • 2Amberg M., Kempter 1., BergstrtBer U., Stapf G., Hartung J., Tetra- hedron: Asymmetry, 2011, 22, 752.
  • 3Wenzel T. J., Chisholm C. D., Prog. Nucl. Magn. Reson. Spectrosc., 2011, 59, 1.
  • 4Wenzel T. J., Wilcox J. D., Chirality, 2003, 15, 256.
  • 5Wang 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.
  • 6Wenzel T. J., Thurston J. E., J. Org. Chem., 2000, 65, 5.
  • 7Lovely A. E., Wenzel T. J., Org. Lett., 2006, 8, 2823.
  • 8Joseph G., Chirality, 2008, 20, 5.
  • 9Thomas R., Frederik N., Naraschewski J. E., Tetrahedron: Asymme- try, 2009, 20, 362.
  • 10Finn M. G., Chiral#y, 2002, 14, 534.

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部