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有机化学
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有机化学 ›› 1990, Vol. 10 ›› Issue (6): 507-512. 上一篇    下一篇

研究论文

手性β-羟基胺在苯硫酚与查尔酮加成反应中的不对称催化作用

邝荣泽;阮素镅;程一枝   

  1. 华南理工大学化学系
  • 发布日期:1990-12-25

Asymmetric addition of thiophenol to chalcone catalyzed by chiral β- hydroxy amines

KUANG RONGZE;RUAN SUMEI;CHENG YIZHI   

  • Published:1990-12-25

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目前, 在胺类催化的不对称亲核加成反应中, 采用的手性催化剂主要是生物碱,但由于生物碱分子中一般含有多个不对称中心, 结构特殊, 只便于研究催化剂结构与不对称催化剂作用的关系, 为此本文从(R)-α-氨基-(-丁醇出发,合成了一系列结构变的手性叔胺-促胺化合物作为手性催化剂, 并在苯硫酚与查耳酮的加成反应中探讨了催化剂结构, 用量及溶剂等因素与不对称催化剂效果的关系。

关键词: 叔胺, 加成反应, 丁醇 P, 红外分光光度法, 元素分析, 质子磁共振谱法, 仲胺, 丁胺 P, 羟胺类, 查耳酮

A no. of chiral amines e.g., EtCH(NR2)CH2OH (R = Me, Et, Pr, Bu, n-pentyl, n-hexyl) were prepared from (R)-2-amino-1-butanol and used as chiral catalysts in the addition of thiophenol to chalcone. An optically active addition product was obtained and its sp. rotation and the half-time of the reaction depended upon whether the carbon atom no. of group R in catalysts was even or odd. Also studied were the effects of solvents and the structure and concentration of catalysts on the asym. catalysis.

Key words: INFRARED SPECTROPHOTOMETRY, TERTIARY AMINE, ELEMENTAL ANALYSIS, ADDITION REACTION, BUTANOL P, PROTON MAGNETIC RESONANCE SPECTROMETRY, SECONDARY AMINE, HYDROXYLAMINES, BUTANAMINE P, CHALCONE

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