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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (10): 1269-1272. 上一篇    

研究简报

氟烷基磺酰氟和(2S,3R)-2,3-二羟基-3-苯基丙酸甲酯的脱水环氧化反应的研究

严兆华*,1, 魏萌1, 田伟生*,2, 官程波1   

  1. (1南昌大学化学系 南昌 330031)
    (2中国科学院上海有机化学研究所 上海 200032)
  • 投稿日期:2010-11-10 修回日期:2010-12-31 发布日期:2011-01-30
  • 通讯作者: 严兆华 E-mail:yanzh@ncu.edu.cn

Study of Cyclodehydration of Methyl (2S,3R)-2,3-Dihydroxy-3- Phenylpropionate with Fluoroalkanesulfonyl Fluoride

Yan Zhaohua*,1,Wei Meng1,Tian Weisheng*,2,Guan Chengbo1   

  1. (1 Department of Chemistry, Nanchang University, Nanchang 330031)
    (2 Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2010-11-10 Revised:2010-12-31 Published:2011-01-30
  • Contact: Zhaohua Yan E-mail:yanzh@ncu.edu.cn

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考察了(2S,3R)-2,3-二羟基-3-苯基丙酸甲酯和几种常用的氟烷基磺酰氟试剂在有机碱存在下的脱水环氧化反应. 实验结果表明, 氟烷基磺酰氟能够诱导(2S,3R)-2,3-二羟基-3-苯基丙酸甲酯发生脱水环氧化反应而生成(2R,3R)-2,3-环氧-3-苯基丙酸甲酯, 得率80%～92%, 且产物的不对映过量(ee)值大于97%. 该方法具有工业化应用前景.

关键词: 氟烷基磺酰氟, (2S,3R)-2,3-二羟基-3-苯基丙酸甲酯, (2R,3R)-2,3-环氧-3-苯基丙酸甲酯, 脱水环氧化反应

The cyclodehydration of methyl (2S,3R)-2,3-dihydroxy-3-phenylpropionate with fluoroalkanesulfonyl fluoride in the presence of an organic base was investigated in detail. The title cyclodehydration resulted in the smooth formation of methyl (2R,3R)-2,3-epoxy-3-phenylpropionate in one step in the yield of 80%～92%, and its enantiomeric excess value is higher than 97%. This new methodology is potentially applicable to industrial manufacturing of methyl (2R,3R)-2,3-epoxy-3-phenylpropionate, a key intermediate for the synthesis of Taxol side chain.

Key words: fluoroalkanesulfonyl fluoride, methyl (2S,3R)-2,3-dihydroxy-3-phenylpropionate, methyl (2R,3R)-2,3-epoxy-3-phenylpropionate, cyclodehydration