Preparation of chiral trans-5-substituted-acenaphthene-1,2-diols by baker’s yeast-mediated reduction of 5-substituted-acenaphthylene-1,2-diones |
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| Authors: | Lixiao Wang Xingyong Wang Jingnan Cui Weimin Ren Nan Meng Jingyun Wang Xuhong Qian |
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| Institution: | 1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, 158 Zhongshan Rd., 116012 Dalian, China;2. State Key Lab. Bioreactor Engineering, Shanghai Key Lab. Chemical Biology, School of Pharmacy, East China University of Science and Technology, PO Box 544, 130 Meilong Road, Shanghai 200237, China |
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| Abstract: | A series of trans-5-substituted-acenaphthene-1,2-diols were obtained in 21–72% yield with 97–100% ee by baker’s yeast-mediated reduction of the corresponding acenaphthylene-1,2-diones, in the presence of DMSO as a co-solvent and under vigorous agitation. The absolute configuration of (?)-trans-5-methoxy-acenaphthene-1,2-diol trans-3b and (?)-trans-5-bromo-acenaphthene-1,2-diol trans-3c was assigned as (S,S) and (?)-trans-5-thiomorpholin-acenaphthene-1,2-diol trans-3d was established as (R,R) by exciton-coupled circular dichroism. |
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