Journal of Guangxi Normal University(Natural Science Edition) ›› 2012, Vol. 30 ›› Issue (3): 207-213.

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Synthesis of Chiral Phosphine Reagents Derived from Maleopimaric Acid and Their Chiral Recognition in 31P NMR Applications

WANG Heng-shan, WU Qiang, YAO Gui-yang, LI Xiu-ying, PAN Ying-ming   

  1. Key Laboratory for the Chemistry and Molecular Engineering ofMedicinal Resources,College of Chemistry and Chemical Engineering,Guangxi Normal University,Guilin Guangxi 541004,China
  • Received:2012-03-23 Online:2012-09-20 Published:2018-12-04

Abstract: Chiral alcohols 5-[(benzyloxy)methyl]-5,9-dimethyl-13β,14β-dihydroxymethyl-16-isopropyl tetracyclo[10.2.2.01,10.04,9] hexadec-15-ene (6) was synthesized in optically pure forms from easilyavailable maleopimaric acid.A comprehensive protocol for the enantiomeric excess assays of mono functional-grouped chiral secondary amine or alcohol has beenestablished by using them as chiral auxiliary for chiral phosphorus derivatizingreagents(CPDA) in 31P NMR tests.Chemical shift difference(Δδp) values are ranging from 0.41 to 0.14 between two diastereoisomers of the CPDAs and the aryl substrates was obtained.

Key words: 31P NMR, maleopimaric acid derived phosphine agents, chiral recognition

CLC Number: 

  • O641
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