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化学学报
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化学学报 ›› 1989, Vol. 47 ›› Issue (7): 662-667. 上一篇    下一篇

研究论文

以(+)-樟脑缩苄胺作中间体对映选择合成(R)-α-取代苄胺

刘桂兰;刘锦初;周昌友;蒋耀忠   

  1. 中国科学院成都有机化学研究所
  • 发布日期:1989-07-15

Enantioselective synthesis of (R)-α-substituted benzyl amines using (+)-camphor imine of benzyl amine as intermediate

LIU GUILAN;LIU JINCHU;ZHOU CHANGYOU;JIANG YAOZHONG   

  • Published:1989-07-15

PDF

395

被引次数

4

本文报道以(+)-樟脑作手性助剂, 苄胺为原料, 二者缩合制得的酮亚胺作中间体3,不对称合成(R)-α-取代苄胺(7)的一条有效新途径。化合物3用丁基锂去质子化提供的锂衍生物4和卤代烷反应, 以较高立体选择性产生烷基化产物6, 化合物6用醋酸羟胺转氨反应后, 获得了光学产率为4.6-90%的(R)-α-取代苄胺(7), 以肟的形式回收(+)-樟脑。

关键词: 苯胺 P, 苯胺 P, 缩合反应, 光学性质, 烷基化, 苄基, 苄基, 丁基锂, 卤代烃, 立体选择性

A new and efficient asym. synthetic route of (R)-a-substituted benzylamines I (R = alkyl cyclohexyl, PhCH2, 4-, 3-MeOC6H4CH2) via ketimine intermediate II, using (+)-camphor as chiral auxiliary reagent and benzylamine as starting material has been reported. Deprotonation of compound II with butyllithium followed by reaction with alkyl halides gave the alkylated products II with high diastereoselectivity. After transamination of II with hydroxylamine acetate the (R)-a-substituted benzylamines I in optical purity of 4.6-90% are obtained and (+)-camphor is recovered as its oxime.

Key words: BENZAMINE P, BENZAMINE P, CONDENSATION REACTION, OPTICAL PROPERTIES, ALKYLATION, BENZYL GROUP, BENZYL GROUP, BUTYLLITHIUM, HALOHYDROCARBON, STEREOSELECTIVITY

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