动态动力学拆分制备（R）-1-氨基茚满有机化学.pdfVIP

DOI: 10.6023/cjoc201311048 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 动态动力学拆分制备(R)-1-氨基茚满 戴晓庭 吴坚平* 孟 枭 徐 刚* 杨立荣 (浙江大学化学工程与生物工程学系 杭州 310027) 摘要 首次采用动态动力学方法成功制备光学纯(R)-1-氨基茚满. 以十二烷基磺酸根离子改性的层状双氢氧化物(LDH) 为载体负载金属钯制备了新型消旋催化剂Pd/LDH-DS, 对其消旋化(S)-1-氨基茚满的反应条件进行了研究, 发现其具有 优越的反应性能; 在此基础上结合脂肪酶 Novozym 435 的反应条件, 最终确定以甲苯为反应溶剂, 戊酸对氯苯酯为酰 基供体, 底物浓度为 82.5 mmol/L, 55 ℃条件下反应 15 h 后制备得到(R)-1-氨基茚满戊酸酯, 产物转化率＞99%, 产物光 学纯度 eeP ＞99%. 关键词 动态动力学; (R)-1-氨基茚满; 消旋催化剂; Novozym 435 Preparation of (R)-1-Aminoindan by Dynamic Kinetic Resolution Dai, Xiaoting Wu, Jianping* Meng, Xiao Xu, Gang* Yang, Lirong (Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027) Abstract Enantiomerically pure (R)-1-aminoindan was firstly prepared by dynamic kinetic resolution. A novel racemization catalyst Pd/layered double-hydroxide-dodecyl sulfate anion (PD/LDH-DS) was prepared and used in the racemization of (S)-1-aminoindan, and the reaction condition was investigated. It was found that the catalyst had superior racemization ability. On this basis, combined with reaction condition of lipase Novozym 435, it was confirmed that toluene was the reaction sol- vent, 4-chlorophenyl valerate was the acyl donor, concentration of substrate was 82.5 mmol/L, reaction temperature was 55 ℃, and the reaction time was 15 h. Under the condition, (R)-1-aminoindan valerate was prepared with excellent ee value ( ＞99%) P