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Acta Chimica Sinica ›› 2011, Vol. 69 ›› Issue (10): 1269-1272. Previous Articles    

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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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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