Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (12): 2545-2550.DOI: 10.6023/cjoc201307007 Previous Articles     Next Articles



李小娜, 周宏勇, 张鹏亮, 王家喜   

  1. 河北工业大学绿色化工与高效节能重点实验室 天津 300130
  • 收稿日期:2013-07-05 修回日期:2013-08-10 发布日期:2013-08-16
  • 通讯作者: 王家喜
  • 基金资助:

    河北省自然科学基金(No. 2011202087)资助项目.

Synthesis of Chiral Amino-acids Derivatives:Silica-gel Promoted Ring Opening of Substituted Aziridines

Li Xiaona, Zhou Hongyong, Zhang Pengliang, Wang Jiaxi   

  1. Hebei Univ Technol, Key Lab Green Chem Technol & High Efficient Energy, TianJin 300130
  • Received:2013-07-05 Revised:2013-08-10 Published:2013-08-16
  • Supported by:

    Project supported by the Natural Science Foundation of Hebei Province (No. 2011202087).

Chiral amine is a kind of important chemicals. Several L-amino acid based chiral diamines and triamines were prepared by ring-opening of substituted aziridines with L-amino acid esters in the matrix of silica without solvent. The ring-opening reactions were promoted by silica and accelerated by ultrasound radiation. The L-amino acid esters reacted with substituted aziridine 2 to give diamine 3 at first, then diamine 3 reacted with aziridine 2 again to form triamine 4. Compared with L-amino acid esters 1, compound 3 had a higher activity. (S)-Methyl pyrrolidine-2-carboxylate (1d) reacted with (R)-2-isopropyl-1-tosylaziridine (5) selectively yielding (S)-methyl 1-[(R)-3-methyl-2-(4-methylphenyl sulfonamide)butyl]pyr-rolidine-2-carboxylate (6b) through the ring opening at 1,3-position of aziridine. All obtained compounds were characterized by 1H NMR, 13C NMR, IR and elemental analysis. 4c was analyzed by X-ray diffraction as well.

Key words: amino acids, substituted aziridine, ring opening, solid phase synthesis, X-ray diffraction