Preparation of chiral trans-5-substituted-acenaphthene-1,2-diols by baker’s yeast-mediated reduction of 5-substituted-acenaphthylene-1,2-diones
作者:Lixiao Wang、Xingyong Wang、Jingnan Cui、Weimin Ren、Nan Meng、Jingyun Wang、Xuhong Qian
DOI:10.1016/j.tetasy.2010.04.048
日期:2010.4
A series of trans-5-substauted-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-12-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. (C) 2010 Elsevier Ltd All rights reserved