Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1811-1816.DOI: 10.6023/cjoc201710003 Previous Articles     Next Articles

Notes

“一锅煮”的化学-酶法合成手性α-卤代芳基醇

杨靖文a, 陈建波b, 王诗婕a, 吴小梅a, 马宝娣a, 徐毅a   

  1. a 上海应用技术大学化学与环境工程学院 上海 201418;
    b 上海师范大学生命与环境科学学院 上海 200234
  • 收稿日期:2017-10-07 修回日期:2018-01-30 出版日期:2018-07-25 发布日期:2018-04-12
  • 通讯作者: 吴小梅, 徐毅 E-mail:xuyi@sit.edu.cn;wuxiaomei@sit.edu.cn
  • 基金资助:

    上海市科委重点基金(No.13430503400)和教育部留学回国人员基金(No.ZX2012-05)资助项目.

“One-Pot” Chemo-enzymatic Synthesis of Chiral α-Halogenated Aryl Alcohols

Yang Jingwena, Chen Jianbob, Wang Shijiea, Wu Xiaomeia, Ma Baodia, Xu Yia   

  1. a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
    b College of Life and Environment Science, Shanghai Normal University, Shanghai 200234
  • Received:2017-10-07 Revised:2018-01-30 Online:2018-07-25 Published:2018-04-12
  • Contact: 10.6023/cjoc201710003 E-mail:xuyi@sit.edu.cn;wuxiaomei@sit.edu.cn
  • Supported by:

    Project supported by the Shanghai Committee of Science and Technology (No. 13430503400) and the Scientific Research Foundation for the Returned Overseas Chinese Scholars, Ministry of Education (No. ZX2012-05).

A novel one-pot chemo-enzymatic method was developed for the preparation of chiral α-halogenated aryl alcohols from cheap aryl ketones. Firstly, the α-halogenated aryl ketones were obtained via halogenation of aryl ketones catalyzed by p-toluenesulfonic acid. Then, α-halogenated aryl ketones was asymmetric reduced to chiral α-halogenated aryl alcohols by adding cell suspension of Rhodotorula sp. AS2.2241 with carbonyl reductase activity into the reaction system without isolating intermediate products. The best reaction condition was optimized for each step and the coupling condition of chemical and biological reaction was studied in detail. It was found that the concentration of organic solvent and the pH value are key factors that affect the enzyme activity of biocatalytic reaction. Under optimized reaction and coupling conditions, four kinds of chiral α-halogenated aryl alcohols were obtained with high yield and high optical purity (yield > 95%, ee > 99%).

Key words: one-pot reaction, chemo-enzymatic synthesis, chiral α-halogenated aryl alcohol, biocatalysis, green chemistry