用高效液相色谱手性固定相法拆分芳香仲醇及芳香乙二醇类手性化合物

Enantiomeric Resolution of Secondary Aromatic Alcohols and Arylethanediols by HPLC on Chiral Stationary Phase

在ChiralcelOD和ChiralcelOJ两支多糖类手性固定相上 ,以各种不同配比的正己烷 -异丙醇为洗脱剂对 38种带有不同取代基的芳香仲醇及芳香乙二醇类手性化合物的对映体进行拆分 .考察了这些外消旋体在这两支手性柱上的色谱行为 .结果表明 ,手性柱对这些化合物的拆分能力与化合物取代基的性质和位置有关 ,这些化合物与手性固定相之间的氢键作用和π π作用是影响手性拆分的重要原因 .拆分方法已应用于潜手性酮不对称还原产物的光学纯度的鉴定 。

Separation of racemic mixtures of thirty-eight secondary aromatic alcohols and arylethanediols with different substituting group was achieved with HPLC by using Chiralcel OD and Chiralcel OJ as chiral stationary phase and hexane/2-propanol mixtures of different ratios as eluents. The chromatographic parameters of these racemates on OD and OJ columns were examined. The results showed enantiomeric resolution ability of the racemic mixtures on these columns was strongly dependent on the site and the property of substituents. The hydrogen bonding and pi-pi interactions between the chiral stationary phase and the polar group of secondary aromatic alcohols and arylethanediols may be responsible for the chiral resolution. This method had been applied to determination of the optical purity of the asymmetric reduction products of prochiral ketones.