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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (9): 1306-1308. 上一篇    下一篇

研究简报

聚乙二醇(400)中的不对称Baylis-Hillman反应

丁益萍，丁一，沈宗旋，李斌，张雅文*   

  1. (苏州大学化学化工学院 江苏省有机合成重点实验室 苏州 215123)
  • 收稿日期:2005-09-05 修回日期:2005-12-06 发布日期:2006-09-11
  • 通讯作者: 张雅文

Asymmetric Baylis-Hillman Reaction in Poly(ethyleneglycol)(400)

DING Yi-Ping,DING Yi,SHEN Zong-Xuan,LI Bin,ZHANG Ya-Wen*   

  1. (Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering,
    Suzhou University, Suzhou 215123)
  • Received:2005-09-05 Revised:2005-12-06 Published:2006-09-11
  • Contact: ZHANG Ya-Wen

PDF

1236

被引次数

15

从易得的L-脯氨酸出发, 方便地合成了氨基醇1. 以聚乙二醇(400)为溶剂, 考察了手性氨基醇1 (30 mol%)在聚乙二醇(400)中催化不对称的Baylis-Hillman反应, 有较好的催化活性和立体选择性, 产率最高达95.4%, ee值最高达54.3%. 手性氨基醇1-聚乙二醇(400)催化体系可方便回收并重复利用, 在前三次循环中, 未发现反应产率和选择性有明显变化.

关键词: 不对称Baylis-Hillman反应, 手性氨基醇, 聚乙二醇(400), 循环使用

Chiral amino alcohol 1 was prepared from L-proline conveniently. In poly(ethyleneglycol) (PEG)(400), this chiral amino alcohol (30 mol%) catalyzes asymmetric Baylis-Hillman reaction effectively. High yields (up to 95.4%) and modest selectivities (up to 54.3% ee) were achieved. The chiral amino alcohol-PEG(400) catalytic system could be easily recovered and reused in the next run. No significant changes in the reaction yields and selectivities were found in the first three runs.

Key words: chiral animo alcohol, recycling, PEG(400), asymmetric Baylis-Hillman reaction