Chemical Research in Chinese Universities ›› 2010, Vol. 26 ›› Issue (1): 50-54.

• Articles • Previous Articles     Next Articles

Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction

GAO Jun-long1, ZHENG Liang-yu2, ZHANG Suo-qin1*, ZHANG Xin-min1, SUN Guo-dong1, QIN Lin1, LI Yao-xian1, LIU Qing-wen1 and LI Xiao-bo1   

  1. 1. College of Chemistry,
    2. Key Laboratory for Molecular Enzymology and Engineering, Ministry of Education, Jilin University, Changchun 130021, P. R. China
  • Online:2010-01-04 Published:2010-03-29
  • Contact: ZHANG Suo-qin. E-mail: suoqin@jlu.edu.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(Nos.20802025 and 20082011).

Abstract:

A series of proline-based amino pyridine dipeptide organocatalysts was synthesized and applied in direct asymmetric intermolecular aldol reaction. These catalysts showed good solubility in organic solvents, good yields (73%―97%) and enantioselectivitives(74%―94%). Among them, dipeptide organocatalyst(2) was found to be the most efficient one for the asymmetric aldol reaction between cyclohexanone and 4-nitrobeznaldehyde. After optimi- zing the catalytic reaction conditions, we found that the catalyst showed high yield(97%), enantioselectivity(e.e., up to 92%) and anti-diastereoselectivity(up to 95:5) at mild room temperature without any additives.

Key words: Proline-based dipeptide; Aldol reaction; Enantioselectivity