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化学学报
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化学学报 ›› 1990, Vol. 48 ›› Issue (2): 168-173. 上一篇    下一篇

研究论文

(+)-樟脑缩苄胺体系的不对称羰基加成反应

刘桂兰;邓金根;蒋耀忠   

  1. 中国科学院成都有机化学研究所
  • 发布日期:1990-02-15

Asymmetric carbonyl addition reaction of (+)-camphor imine derived from benzylamine

LIU GUILAN;DENG JINGEN;JIANG YAOZHONG   

  • Published:1990-02-15

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本文通过(+)-樟脑缩苄胺(I)与不同醛、酮的不对称加成, 经转氨合成了1,2-取代-2-氨基乙醇(2), 反应的非对映选择性经NMR测定为16-70%de.; 苏式、赤式异构体的含量比由HPLC法测定, 其值接近1, 由于立体位阻的原因加成反应发生在锂化物3的Re面。

关键词: 核磁共振谱法, 羰基合成, 加成反应, 酮, 樟脑, 非对映立体异构, 模外相边界层, 氨基乙醇 P, 苄胺, 不对称反应

The 1,2-substituted 2-aminoethanol derivatives I (R = Ph, 4-MeOC6H4, 3,4-(MeO)C6H7; R' = H, Me, Ph) were synthesized from the asym. addition of (+)-camphor imine II derived from benzylamine to a variety of aldehydes or ketones RCOR'. The diastereoselectivities ranging from 16-70% were determine by NMR spectra of addition products III.

Key words: NMR SPECTROMETRY, CARBONYL SYNTHESIS, ADDITION REACTION, KETONE, CAMPHOR, DIASTEROISOMERISM, EXTERNAL PHASE BOUNDARY FILM, AMINO ETHANOL P, BENZENEMETHANAMINIUM

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