手性氨基酸衍生物的合成：硅胶促进的取代氮丙啶的开环反应
收稿日期: 2013-07-05
修回日期: 2013-08-10
网络出版日期: 2013-08-16
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
Received date: 2013-07-05
Revised date: 2013-08-10
Online published: 2013-08-16
Supported by
Project supported by the Natural Science Foundation of Hebei Province (No. 2011202087).
李小娜 , 周宏勇 , 张鹏亮 , 王家喜 . 手性氨基酸衍生物的合成：硅胶促进的取代氮丙啶的开环反应[J]. 有机化学, 2013 , 33(12) : 2545 -2550 . DOI: 10.6023/cjoc201307007
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.
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