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有机催化剂催化的不对称oxo-Michael/Mannich串联反应研究

Study on Asymmetric oxo-Michael/Mannich Domino Reaction Catalyzed by Organocatalysts

【作者】 谌均

【导师】 彭云贵;

【作者基本信息】 西南大学 , 有机化学, 2011, 硕士

【摘要】 本文设计、合成了一系列新型多功能催化剂,并对其合成方法进行了研究。将这些催化剂用于催化水杨醛衍生的对甲苯磺酰亚胺与β-硝基苯乙烯的不对称oxo-Michael/Mannich串联反应,筛选出催化活性和对映选择性较好的多功能催化剂4b。并系统考察了反应溶剂、反应温度、催化剂量等因素对反应活性和选择性的影响,结果表明:反应以1,2-二氯乙烷作溶剂,10 mol%催化剂量,在-40℃下进行可获得85%的收率,e.e.值能达到87%,d.r.值高达99:1。

【Abstract】 In this thesis, a series of novel multi-functional catalysts have been designed and synthesized, and their synthetic methodologies have also been studied. These multi-functional organocatalysts were further applied to catalyze the asymmetric oxo/Michael-Mannich domino reaction of salicyl N-tosylimine withβ-nitrostyrene. It was found that the multifunctional catalyst 4b could give good reactivity and enantioselectivity. The influences of reaction solvent, temperature, catalyst loading and etc on the reactivity and selectivity have been systematically investigated and the results have demonstrated that good yield (>85%), enantioselectivity (87% e.e.) and high diastereoselectivity (99:1 d.r.) were achieved when the reaction proceeded in 1,2 dichloroethane at-40℃with 10 mol% catalyst 4b.

  • 【网络出版投稿人】 西南大学
  • 【网络出版年期】2011年 09期
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