Citation: Yang Jingwen, Chen Jianbo, Wang Shijie, Wu Xiaomei, Ma Baodi, Xu Yi. "One-Pot" Chemo-enzymatic Synthesis of Chiral α-Halogenated Aryl Alcohols[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1811-1816. doi: 10.6023/cjoc201710003 shu

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

Yang Jingwen ^a ,
Chen Jianbo ^b ,
Wang Shijie ^a ,
Wu Xiaomei ^a,, ,
Ma Baodi ^a ,
Xu Yi ^a,,

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

Corresponding author: Wu Xiaomei, wuxiaomei@sit.edu.cn Xu Yi, xuyi@sit.edu.cn
Received Date: 7 October 2017
Revised Date: 30 January 2018
Available Online: 12 July 2018
Fund Project: the Shanghai Committee of Science and Technology 13430503400the Scientific Research Foundation for the Returned Overseas Chinese Scholars, Ministry of Education ZX2012-05Project 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)

Figures(2)

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%).
- one-pot reaction,
- chemo-enzymatic synthesis,
- chiral α-halogenated aryl alcohol,
- biocatalysis,
- green chemistry
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