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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (08): 1416-1422. 上一篇    下一篇

研究论文

C2对称性有机小分子催化的高对映选择性Aldol反应

顾 庆; 江玲霞; 王 琼; 伍新燕*   

  1. (华东理工大学教育部结构可控先进功能材料及其制备重点实验室 精细化工研究所 上海 200237)
  • 收稿日期:2007-11-13 修回日期:2008-03-05 发布日期:2008-08-18
  • 通讯作者: 伍新燕

Highly Enantioselective Aldol Reaction Catalyzed by C2 Symmetric Organocatalyst

GU, Qing ; JIANG, Ling-Xia; WANG, Qiong ; WU, Xin-Yan*

  

  1. (Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237)
  • Received:2007-11-13 Revised:2008-03-05 Published:2008-08-18
  • Contact: WU, Xin-Yan

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以环己酮与4-硝基苯甲醛直接不对称Aldol缩合为模型反应, 对一系列具有C2对称性的有机小分子催化剂进行了考察, 其中(2S,5S)-吡咯烷-2,5-二羧酸的不对称催化效果最好. 在10 ℃下, 以DMSO为溶剂, 30%摩尔分数催化剂用量, 研究了多个取代芳香醛和环己酮的不对称催化Aldol反应, 对映选择性为87%～99% ee.

关键词: 直接Aldol反应, 不对称催化, 环己酮, 有机催化剂

Several C2 symmetric molecules were tested as organocatalysts for the direct catalytic asymmetric aldol reaction of cyclohexanone with 4-nitrobenzaldehyde. (2S,5S)-Pyrrolidine-2,5-dicarboxylic acid afforded the best results for this transformation. The reaction of a series of aromatic aldehydes with cyclohexanone was carried out in DMSO using a catalyst loading of 30 mol% at 10 ℃, and the aldol adducts were obtained in 87%～99% ee.

Key words: direct aldol reaction, organocatalyst, cyclohexanone, enantioselective catalysis