Efficient Synthesis of (R)-2-Chloro-1-(3-chlorophenyl)ethanol by Permeabilized Whole Cells of Candida ontarioensis

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• 作者：Ye NI ; ^{yni@jiangnan.edu.cn} ; Beihua ZHANG ; Zhihao SUN
• 关键词：(R)-2-chloro-1-(3-chlorophenyl)ethanol ; asymmetric reduction ; cetyltrimethylammonium bromide ; permeability ; Candida ontarioensis
• 刊名：Chinese Journal of Catalysis
• 出版年：2012
• 期刊代码：3_18722067
• 类别：ce
• 出版时间：April-June, 2012
• 卷：33
• 期：4-6
• 页码：681-687
• 文件大小：154 K

摘要

(R)-2-Chloro-1-(3-chlorophenyl)ethanol is a key pharmaceutical intermediate in the synthesis of ₃-adrenoceptor receptor (₃-AR) agonists. The asymmetric reduction of 2-chloro-1-(3-chlorophenyl)ethanone to (R)-2-chloro-1-(3-chlorophenyl)ethanol catalyzed by resting cells of Candida ontarioensis was studied. At a substrate concentration of 10 g/L, the microbial cells showed excellent catalytic activity under the optimum reaction conditions, giving the product in 99.9%ee and 99.0%yield. After cetyltrimethylammonium bromide-pretreatment, the activity of permeabilized Candida ontarioensis cells was increased by more than 2-fold and the product could be produced over the significantly shortened reaction period of 24 h in 99.9%ee and 97.5%yield at a substrate concentration of 30 g/L. This work provides a practical approach for the efficient preparation of the important chiral intermediate (R)-2-chloro-1-(3-chlorophenyl) ethanol.