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含松香骨架的手性氮杂冠醚的合成及其在不对称Michael加成反应中的应用
Synthesis and Catalytic Activities of Chiral Azacrown Ethers Derived from Rosin
【摘要】 以松香为原料,合成了4个手性氮杂冠醚:N-脱氢松香基单氮杂-12-冠-4、N-脱氢松香基单氮杂-15-冠-5、N-脱氢松香基单氮杂-18-冠-6和N-降解脱氢松香基单氮杂-12-冠-4,并用于催化不对称查尔酮Michael加成反应,发现这些手性氮杂冠醚可以有效地催化2-硝基丙烷与查尔酮的不对称Michael加成,Michael加成产物ee最高达35%.
【Abstract】 Four chiral azacrown ethers were synthesized from rosin: N-dehyroabietyl monoaza-12-crown-4,N-dehyroabietyl monoaza-15-crown-5,N-dehyroabietyl monoaza-18-crown-6 and N-degrading-dehyroabietyl monoaza-12-crown-4,which were employed as phase-transfer catalysts in asymmetric Michael addition of 2-nitropropane to chalcone,affording the corresponding Michael addition products up to 35% ee.
【关键词】 松香;
合成;
手性氮杂冠醚;
查尔酮;
不对称Michael加成;
【Key words】 rosin; synthesis; chiral azacrown ether; chalcone; asymmetric Michael addition;
【Key words】 rosin; synthesis; chiral azacrown ether; chalcone; asymmetric Michael addition;
【基金】 国家自然科学基金(No.20442005);国家自然科学基金(Nos.20362002,20762001)资助项目
- 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,2008年07期
- 【分类号】TQ203.2
- 【被引频次】13
- 【下载频次】366