1-叠氮-2-苯并[f]茚满醇的四个光学活性异构体的合成

Synthesis of Four Optical Active Stereoisomers of 1-Azidobenz[f]indan-2-ol

以1-苯并[f]茚为原料,合成了反式外消旋体1-叠氮-2-苯并[f]茚满醇[(±)-trans-1];(±)-trans-1经脂肪酶催化拆分得到两个反式对映异构体(1a和1c);1a和1c通过Mitsunobu反应构型转化得到两个顺式异构体(1b和1d)。其结构经1HNMR和13C NMR表征;4个光学活性异构体1a^1d的光学纯度均为99%e.e.。

（ ± ）-trans-l-Azidobenz[fjindan-2-ol[ （ ± ）-trans-1] was synthesized from 1-benz[f]indene. （± ）-trans-1 was resolved to obtain two trans-enantiomers（1a and 1c） using lipase PS as a catalyst, 1a and 1c were translated into two cis-enantiomers（1b and 1d） by Mitsunobu reaction. The structures were characterized by ^1H NMR and ^13C NMR. The optical purities of 1a - 1d were 99% e.e..