Synthesis of Optically Active Compounds Having Pentafluorophenyl Group - The Structure and Function

五氟醚组显示两个电子-具有丰富的电子分子的特性和可堆叠性。However，有几份关于功能材料应用的报告。我们期望手性五氟醚组含有化合物的化合物将被用于液体晶体和分子识别材料。脂质脂质体-2-催化的动力学溶液。（五氟苯基）乙腈（1）在0℃下具有影响力的光学活性（R）-1与96%的ee，其（S）-乙酸衍生物与98%的ee。间接地，我们成功地转换了（R）-1至（1 R，2 R）-二（五氟苯基）乙烷-1，2-二醇（（1 R，2 R）-（2））与94%的ee，（S）-1至（1 S， 2S）-2与87%的ee，我们发现了TMSCI增加了TMSCI的添加剂，将NaBH D24-D2减少了微量中介质和同样地抑制了种族化。我们也合成了光学活性的二醇和氨基醇，如1-（五氟苯基）-2-苯甲酸-1，2-二醇，2-氨基-1，2-二（五氟苯基）乙醇和2-氨基-1-（五氟苯基）-2-苯甲酸醇，根据类似方法计算。Furthermore，我们确认五氟苯基组和富含电子的芳香组之间的堆叠相互作用是X射线晶体结构分析和核磁共振测量的指标。

Pentafluorophenyl group shows both electron-withdrawing property and stucking ability for electron-rich aromatic molecules. However, there is few report on its application to functional materials. We expected that chiral pentafluorophenyl group-containing compounds will be useful for liquid crystals and molecular recognition materials.The lipase LIP-catalyzed kinetic resolution of 2-hydroxy-2-(pentafluorophenyl)acetonitrile (1) at 0℃ afforded optically active (R)-1 with 96% ee and its (S)-acetate derivative with 98% ee. Subsequently, we successfully converted (R)-1 to (1R, 2R)-bis(pentafluorophenyl)ethane-1, 2-diol ((1R, 2R)-(2)) with 94% ee and (S)-1 to (1S, 2S)-2 with 87% ee. We found that the addition of TMSCI accelerated the NaBHィイD24ィエD2 reduction of the imine intermediate and simultaneously suppressed the racemization. We also synthesized optically active diols and amino alcohols such as 1-(pentafluorophenyl)-2-phenylethane-1, 2-diol, 2-amino-1, 2-bis(pentafluorophenyl)ethanol, and 2-amino-1-(pentafluorophenyl)-2-phenylethanol according to the similar method. Furthermore, we confirmed the stucking interaction between the pentafluorophenyl group and electron-rich aromatic groups by means of the X-ray crystal structure analysis and NMR measurements.