An efficient chiral phosphorus derivatizing agent for the determination of the enantiomeric excess of chiral alcohols and amines by 31P NMR spectroscopy

The chiral phosphorus derivatizing agent (CDA) 1 was prepared from optically pure (S)-1,1-bis-2-naphthol. It was first used in the determination of the enantiomeric excess of chiral alcohols and amines by means of 31P NMR spectroscopy. It showed that, for the chiral aromatic alcohols, no apparent kinetic resolution was noted and good base-line separation was observed. Furthermore, the chemical shift difference (Δδ) of 31P NMR spectroscopy was much larger than those determined by the use of other chiral phosphorus derivatizing agents reported previously. However, for aliphatic alcohols, it showed not only obvious kinetic resolutions but incomplete base-line separation. Moreover, we also found that the use of CDA 1 was suitable for the determination of enantiomeric excess of chiral primary amines. © 2002 John Wiley & Sons, Inc. Heteroatom Chem 13:93–95, 2002; DOI 10.1002/hc.10018

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