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Chemical Research in Chinese Universities ›› 2012, Vol. 28 ›› Issue (6): 1003-1010.

• Articles • Previous Articles     Next Articles

Chiral Diamine-catalyzed Asymmetric Aldol Reaction

LI Hui, XU Da-zhen, WU Lu-lu, WANG Yong-mei   

  1. State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China
  • Received:2011-11-16 Revised:2012-01-13 Online:2012-11-25 Published:2012-11-09
  • Contact: WANG Yong-mei E-mail:ymw@nankai.edu.cn
  • Supported by:

    Supported by the National Basic Research Program of China(No.2010CB833300) and the Research Fund for the Doctoral Program of Higher Education, China(No.20090031110019).

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Abstract:

A highly efficient catalytic system composed of a simple and commercially available chiral primary diamine (1R,2R)-cyclohexane-1,2-diamine(6) and trifluoroacetic acid (TFA) was employed for asymmetric Aldol reaction in em-PrOH at room temperature. A loading of 10%(molar fraction) catalyst 6 with TFA as a cocatalyst could catalyze the Aldol reactions of various ketones or aldehydes with a series of aromatic aldehydes, furnishing Aldol pro- ducts in moderate to high yields(up to >99%) with enantioselectivities of up to >99% and diastereoselectivities of up to 99:1.

Key words: Aldol reaction, Chiral primary diamine, Asymmetric organocatalysis