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Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (05): 922-926. Previous Articles     Next Articles

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两种邻、间手性二醇的区域选择性取代反应研究

杨运旭*，季兴跃，刘世香，李文军，吴朝辉   

  1. (北京科技大学应用科学学院化学系 北京 100083)
  • 收稿日期:2007-06-20 修回日期:2008-01-10 发布日期:2008-05-20
  • 通讯作者: 杨运旭

Regioselective Substitution Reaction of Two Chiral 1,2-/1,3-Diols

YANG Yun-Xu*,JI Xing-Yue,LIU Shi-Xiang,LI Wen-Jun,WU Zhao-Hui   

  1. (Department of Chemistry, School of Applied Science, University of Science and Technology, Bei-jing 100083)
  • Received:2007-06-20 Revised:2008-01-10 Published:2008-05-20
  • Contact: YANG Yun-Xu

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The regioselective substitution of two chiral 1,2-/1,3-diols was studied in this paper. (R)-(－)-Butane-1,3-diol (1) was firstly treated with SOCl2 to form a cyclo-sulfurous ester intermediate (5), which then reacted with thiophenol in the presence of 2% Na2CO3 to regioselectively afford (R)-(－)-3-hydroxybutyl phenylsulfide (3). Similarly, (S,R)-(＋)-1-(6-fluoro-2-chromanyl)-1,2-ethanediol (6) reacted with SOCl2 and subsequently with benzylamine to form (S,R)-(－)-2-(benzylamino)-1-(6-fluoro-2-chromanyl)-ethanol (8). This method has advantages of high regioselectivity, high yield and high ee values.

Key words: chiral, regioselectivity, substitution reaction, diol