Chinese Journal of Organic Chemistry >
“One-Pot” Chemo-enzymatic Synthesis of Chiral α-Halogenated Aryl Alcohols
Received date: 2017-10-07
Revised date: 2018-01-30
Online published: 2018-04-12
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%).
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
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