有机化学 ›› 1995, Vol. 15 ›› Issue (5): 550-554. 上一篇    下一篇

研究论文

由(1R, 2S)-麻黄碱制备的硼杂恶唑烷催化甲硼烷不对称还原苯乙酮

黄世文;单自兴;段标;赵德杰   

  1. 武汉大学化学系
  • 发布日期:1995-10-25

Asymmetric reduction of acetophenone with borane catalyzed by chiral oxazaborolidine prepared from (1R, 2S)-epherdrine

HUANG SHIWEN;SHAN ZIXING;DUAN BIAO;ZHAO DEJIE   

  • Published:1995-10-25

由(1R, 2S)-麻黄碱制得了五个新的手性硼杂恶唑烷1~5, 它们催化甲硼烷不对称还原苯乙酮, 获得了高产率的具有38.5~72.4%e. e.的R-1-苯基乙醇。讨论了催化剂的结构-活性关系及反应参数(催化剂用量、反应温度)对还原对应对映选择性的影响。

关键词: 苯基乙醇, 恶唑 P, 催化, 苯乙酮, 甲硼烷, 硼杂环化合物, 麻黄碱, 还原反应

Some new oxazaborolidines 1~5, Prepared from the reaction of (1R, 2S)-epherdrine and BH3.SMe2 or RB(OH)2, Serve as chiral catalysts for the asymmetric reduction of acetophenone with borane to give the (R)-1-phenylethanol with 38.5~72.4% e.e. in high yield. The structure- reaction relationship of the catalysts and the effect of reaction parameters (the amount of catalyst and reaction temperature) on enantioselectivity of the reduction are discussed.

Key words: CATALYSIS, ACETOPHENONE, BORANE, BORON HETEROCYCLIC COMPOUNDS, EPHEDRINE, PHENYLETHANOL, REDUCTION REACTION

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