Lipase-catalyzed transesterification of 2-hydroxy-2-(pentafluorophenyl)acetonitrile leading to (1R,2R)- and (1S,2S)-bis(pentafluorophenyl)ethane-1,2-diol
Lipase-catalyzed transesterification of 2-hydroxy-2-(pentafluorophenyl)acetonitrile leading to (1R,2R)- and (1S,2S)-bis(pentafluorophenyl)ethane-1,2-diol
复制标题
脂肪酶催化 2-羟基-2-(五氟苯基)乙腈发生酯交换反应生成 (1R,2R)- 和 (1S,2S)-双(五氟苯基)乙烷-1,2-二醇
作者：
Sakai;Miki;Tsuboi;Takeuchi;Ema;Uneyama;Utaka
以脂肪酶催化的(1R，2R)-和(1S，2S)-1，2-bis(pentafluorophenyl)ethane-1，2-diol(2)为主要中间体，合成了光学纯的(1R，2R)-和(S)-2-hydroxy-2-(pentafluorophenyl)acetonitrile(1)。(S)-2转变为(S)-α-氰基-2，3，4，5，6-五氟苯甲基(S)-6-methoxy-alpha-methyl-2-naphthaleneacetate(S，S)-9后，通过X射线结构分析确定了其绝对构型。此外，(S，S)-9的晶体结构具有有趣的有序堆积模式，表现出相邻分子的五氟苯基和6-甲氧基萘基之间存在面对面的堆积作用和端到端的平行接触。
Optically pure (1R,2R)- and (1S,2S)-1,2-bis(pentafluorophenyl)ethane-1,2-diol (1) were synthesized from key intermediates (R)- and (S)-2-hydroxy-2-(pentafluorophenyl)acetonitrile (2), both of which were prepared by the lipase LIP-catalyzed transesterification (E = 465). The absolute configuration of (S)-2 was determined by X-ray structural analysis after transformation into (S)-alpha-cyano-2,3,4,5,6-pentafluorobenzyl (S)-6-methoxy-alpha-methyl-2-naphthaleneacetate (S,S)-9. In addition, the crystal structure of (S,S)-9 has an interesting well-ordered packing pattern which shows face-to-face stacking interactions and end-to-end parallel contacts between the pentafluorophenyl and 6-methoxynaphthyl groups of the adjacent molecules.