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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (04): 488-493. 上一篇    下一篇

研究论文

手性磺酸基联萘(并冠)醚的合成及水相中直接催化三组分Mannich反应

季凤英a，陈永飞a，陈玉红a，蔡继文*,a,b   

  1. (a中山大学化学与化学工程学院 广州 510275)
    (b中山大学药学院 广州 510080)
  • 收稿日期:2006-03-07 修回日期:1900-01-01 发布日期:2007-03-29
  • 通讯作者: 蔡继文

Syntheses of Chiral Sulfobinaphtho-Crown Ethers and Their Catalytic Properties for the Three-Component Mannich Reaction in Water

JI Feng-Yinga, CHEN Yong-Feia, CHEN Yu-Honga, CAI Ji-Wen*,a,b   

  1. (a School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guang-zhou 510275)
    (b School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510080)
  • Received:2006-03-07 Revised:1900-01-01 Published:2007-03-29
  • Contact: CAI Ji-Wen

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1192

被引次数

11 | 3

由1,1'-联-2-萘酚经Williamson合成法及与二甘醇/三甘醇单/双对甲苯磺酸酯反应, 制得10个联萘(并冠)醚, 用氯磺酸磺化, 分别得到10个6,6'二磺酸基联萘(并冠)醚(3a～3f, 6a～6d). 将手性磺酸基联萘(并冠)醚作为Brønsted酸催化剂, 水相中直接催化苯胺、苯甲醛和环己酮三组分Mannich反应, 获得高化学收率(90%～99%)和非对映选择性产物, 其中(R)-6,6'-二磺酸基联萘并-20-冠-6的非对映选择性de 98%. 催化苯胺/取代苯胺、苯甲醛和苯乙酮的反应, 结果显示反应与催化剂和底物分子结构、反应温度及反应时间有关. 催化剂容易回收, 重复使用多次活性基本不减.

关键词: 1,1'-联-2-萘酚, Mannich反应, 冠醚, 磺化, 手性催化剂, 合成

Ten 6,6'-disulfobinaphtho-crown ethers were synthesized via sulfonization of the corresponding crown ethers. Chiral sulfobinaphtho-crown ethers were used to catalyze the 3-component Mannich reaction of analine, benzaldehyde and cyclohexanone in aqueous media and show excellent yield and diastereoselec-tivity up to de 98%. Investigation into the reactions of analine/substituted analine, benzaldehyde and hypnone demonstrates that the molecular structures of the catalysts and the substrate compounds, as well as the reaction temperature and time can influence the catalytic results.

Key words: sulfonization, chiral catalyst, Mannich reaction, synthesis, crown ether, 1,1'-bi-2-naphthol (BINOL)