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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (9): 1400-1404. 上一篇    下一篇

研究简报

蒽酮与β-硝基苯乙烯的不对称Michael加成反应

何天雄, 伍新燕   

  1. (华东理工大学精细化工研究所 结构可控先进功能材料及其制备教育部重点实验室 上海 200237)
  • 收稿日期:2009-11-04 修回日期:2010-04-16 发布日期:2010-04-30
  • 通讯作者: 伍新燕 E-mail:xinyanwu@ecust.edu.cn
  • 基金资助:

    国家级.国家自然科学基金

Enantioselective Organocatalytic Michael Addition of Anthrone to Ni-troalkenes

HE Tian-Xiong, WU Xin-Yan   

  1. (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237)
  • Received:2009-11-04 Revised:2010-04-16 Published:2010-04-30

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不对称催化Michael加成反应是一类重要的形成碳—碳键的反应, 以蒽酮作为亲核试剂的不对称Michael反应报道甚少. 以手性伯胺硫脲作为催化剂, 对蒽酮与硝基苯乙烯的不对称有机催化Michael加成反应进行了研究. 实验结果表明, 所用的伯胺硫脲均具有较好的催化活性(80%～95%收率), 其中硫脲4a得到了较高的对映选择性. 对反应条件进行优化后, 以乙醚为溶剂, 使用5%摩尔分数催化剂4a和苯甲酸, 研究了多个硝基苯乙烯类底物和蒽酮的Michael加成反应, 获得了优异的化学收率(95%～98%)和较好的对映选择性(最高86% ee).

关键词: Michael加成反应, 不对称有机催化, 伯胺硫脲, 蒽酮

The enantioselective organocatalytic Michael addition of anthrone to nitroalkenes was investigated using chiral primary amine thiourea. All the screened thioureas based on (1R,2R)-1,2-di-phenylethane-1,2-diamine could promote the reaction between anthrone and β-nitrostyrene (80%～95% yields), and the thiourea 4a afforded good enantioselectivity. Treatment of anthrone with dif-ferent β-nitrostyrenes in the presence of 5 mol% organocatalyst 4a and 5 mol% benzoic acid in ether provided the desired Michael products with excellent chemical yields (95%～98% yields) and good enantioselectivities (up to 86% ee).

Key words: Michael addition, enantioselective organocatalysis, primary amine thiourea, anthrone