关键词: 氨基酸, 取代氮丙啶, 开环反应, 固相合成, X射线衍射

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