化学学报 ›› 1992, Vol. 50 ›› Issue (8): 817-821. 上一篇    下一篇

研究论文

光学活性α-取代(2-吡啶基)甲胺的对映选择性合成

宓爱巧;肖勋;吴兰均;蒋耀忠   

  1. 中国科学院成都有机化学研究所
  • 出版日期:1992-08-15 发布日期:1992-08-15

Enantioselective syntheses of optically active a-substituted-(2-pyridyl)methyiamines

MI AIQIAO;XIAO XUN;WU LANJUN;JIANG YAOZHONG   

  • Online:1992-08-15 Published:1992-08-15

以2-羟基蒎烷-3-酮为手性助剂, 与2-氨甲基吡啶缩合得到中间体酮亚胺, 经去质子化、不对称烷基化、转胺反应得到光学活性α-取代(2-吡啶基)甲胺, 对映体过量值为89-98%。并提出了过渡态模型, 对对映选择性合成反应作了较为合理的解释。

关键词: 生物碱, 红外分光光度法, 质谱法, 核磁共振谱法, 光学活性, 吡啶基甲胺, 羟基蒎烷酮, 氨基吡啶

Optically active a-substituted (2-pyridyl)methylamines I (R = Me, Me2CH, allyl, PhCH2, 4-MeOC6H4CH2) were obtained by using 2-hydroxypinan-3-one as a chiral auxiliary, condensed with 2-aminomethyl pyridine to form a chiral ketimine and followed by asym. alkylation with different RX (X = Br, Cl, iodo) and removal of the auxiliary. The e.e. values of I were 89-98%. The transition model was successful in explaining the results.

Key words: ALKALOID, INFRARED SPECTROPHOTOMETRY, MASS SPECTROGRAPHY, NMR SPECTROMETRY, AMINOPYRIDINE

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