上海大学学报(自然科学版)

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光学活性胺的不对称合成

王欣,浦家齐   

  1. 上海大学 理学院,上海 200444
  • 收稿日期:2006-11-17 修回日期:1900-01-01 出版日期:2008-02-28 发布日期:2008-02-28
  • 通讯作者: 浦家齐

Asymmetrical Synthesis of Optical Active Amines

WANG Xin, PU Jia-qi   

  1. College of Sciences, Shanghai University, Shanghai 200444, China
  • Received:2006-11-17 Revised:1900-01-01 Online:2008-02-28 Published:2008-02-28
  • Contact: PU Jia-qi

摘要: 采用前手性的酮1a-d为原料,R-或S-α-苯乙胺为手性试剂,经3步反应合成光学活性的胺类化合物4a-d.全部合成过程不用昂贵试剂,不用加压,立体选择性在中等以上,总产率39%~50%.亚胺化反应的时间长短对产物的E/Z选择性有明显影响,降低还原温度有助于提高立体选择性.

关键词: α-苯乙胺, 胺类化合物, 不对称合成, 甲酸铵, 手性化合物

Abstract: Optical active amines 4a-d were prepared in three steps from prochiral ketones 1a-d using R- or S-α-phenylethylamine as chiral source. All reactions were carried out under atmospheric pressure, and expensive chemicals were not used. Medium or good stereoselectivities were found. Over all yields were 39%~50%. Reaction time of imination plays an important role for E/Z selectivity of product 2a-d. Stereoselectivity would be improved if much lower temperature were used in the reduction.

Key words:
ammonium formate,
amine, chiral compound, α-phenylethylamine, asynmmetric synthesis

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