Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (1): 68.

• Articles • Previous Articles     Next Articles

Synthesis and Asymmetric Henry Reaction of Menthyl Arylglyoxylate

XIANG Ji-Ming1,2, LI Bao-Lin1*   

  1. 1. School of Chemistry and Materials Science, Key Laboratory of Medicinal Plant Resource & Natural Pharmaceutical Chemistry of Ministry of Education, Shaanxi Normal University, Xi′an 710062, China;
    2. Department of Chemistry and Chemical Engineering, Ankang University, Ankang 725000, China
  • Received:2009-04-07 Online:2010-01-10 Published:2010-01-10
  • Contact: LI Bao-Lin. E-mail: baolinli@snnu.edu.cn
  • Supported by:

    教育部科学技术研究重点项目(批准号: 105153)资助.

Abstract:

In the presence of titanium(Ⅳ) tetraethoxide, eight chiral menthyl arylglyoxylates were prepared by transesterification of ethyl arylglyoxylates and the natural (1R,2S,5R)-(-)-menthol. Seven new menthyl (2R)-2-hydroxy-2-aryl-3-nitropropionates were synthesized by the Henry reaction of menthyl arlglyoxylates and nitromethane. The structures of the products were characterized by IR, 1H NMR, 13C NMR spectroscopy, MS and elemental analysis. The diastereoselectivities were analyzed by HPLC with chiral column. The diastereomeric excess(d.e.) of the condensation reactions were between 46.5%—64.2%, achieve diastereoselectivities control to the structure.

Key words: α-Arylketoester; L-Menthol; Transesterification; Asymmetric Henry reaction

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