Acta Chimica Sinica ›› 1989, Vol. 47 ›› Issue (7): 662-667. Previous Articles     Next Articles

Original Articles

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

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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