Production of Chiral Aromatic Alcohol by Asymmetric Reduction with Vegetable Catalyst

• Published in: Chinese journal of chemical engineering 2010-12, Vol.18 (6), p.1029-1033
• Main Authors: CHANG, Xu, YANG, Zhonghua, ZENG, Rong, YANG, Gai, YAN, Jiabao
• Format: Article
• Language: English
• Subjects: Acetophenone; Alcohols; Apples; asymmetric reduction; Asymmetry; bioreduction; Carrots; Catalysts; chiral alcohol; plant catalysis; Reduction; Sweets; Vegetables; 不对称催化还原; 不对称还原反应; 手性醇; 最佳反应条件; 生物催化剂; 芳香醇; 蔬菜产品
• ISSN: 1004-9541; 2210-321X
• DOI: 10.1016/S1004-9541(09)60164-6

Chiral aromatic alcohols are the key chiral building block for many important enantiopure pharmaceu-ticals. In this work,we studied asymmetric reduction of prochiral aromatic ketone to produce the corresponding chiral alcohol using vegetables as the biocatalyst. Acetophenone was chosen as the model substrate. The results in-dicate that acetophenone can be reduced to the corresponding chiral alcohols with high enantioselectivity by the chosen vegetables,i.e. apple（Malus pumila）,carrot（Daucus carota）,cucumber（Cucumis sativus）,onion（Allium cepa）,potato（Soanum tuberosum）,radish（Raphanus sativus）,and sweet potato（Ipomoea batatas） . In the reaction,R-1-phenylethanol is produced with apple,sweet potato and potato as the catalyst,while S-1-phenylethanol is the product with the other vegetables as the catalyst. In term of the enantioselectivity and reaction yield,carrot（D. ca-rota） is the best catalyst for this reaction. Furthermore,the reaction characteristics were studied in detail using car-rot（D. carota） as the biocatalyst. The effects of various factors on the reaction were investigated and the optimal reaction conditions were determined. Under the optimal reaction conditions（reaction time 50 h,substrate concen-tration 20 mmol·L-1,reaction temperature 35 °C and pH 7）,95% of e.e.（to S-1-phenylethanol） and 85% chemical yield can be obtained. This work extends the biocatalyst for the asymmetric reduction reaction of prochiral aromatic ketones,and provides a novel potential route to produce enantiopure aromatic alcohols.