高等学校化学学报 ›› 1984, Vol. 5 ›› Issue (6): 807.

• 论文 • 上一篇    下一篇

甲基乙基丙二酸的不对称酯化反应

朱兴沛, 吴永仁, 尹承烈   

  1. 北京师范大学化学系
  • 收稿日期:1983-01-07 出版日期:1984-12-24 发布日期:1984-12-24

The Asymmetric Esterification of Ethylmethylmalonic Acid

Zhu Xingpei, Wu Yongren, Yin Chenglie   

  1. Department of Chemistry, Beijing Normal University, Beijing
  • Received:1983-01-07 Online:1984-12-24 Published:1984-12-24

摘要: 由甲基乙基丙二酸与l-薄荷醇的单酯化反应产物(Ⅰ)经酰氯(Ⅱ)转变为酰胺(Ⅲ),(Ⅲ)经皂化得到部分光学活性的甲基乙基丙二酸氢酰胺(Ⅳ),(Ⅳ)经Hoffmann降解得到部分光学活性的2-甲基-2-氨基丁酸(V).

Abstract: Ethylmethylmalonic acid reacted with l-menthol to form the diastereo-meric l-menthyl hydrogen ethylmethylmalonates (Ⅰ).From(Ⅰ)the diaster-eomeric l-menthyl ethylmethylmalonamides(Ⅲ) were obtained in nearly quantitative yield. To saponify the amides(Ⅲ) with alkali, the partially optically active ethylmethylmalonanic acid(Ⅳ) were produced in 70% yield. (Ⅲ) were degraded to partially optically active a-amino-methylethylacetic acid (Ⅴ) (V,8.8%e.e S - (+) -isomer)by the Hoffmann degradaton.In DMFthe monobrucine salts of ethylmethylmalonic acid reacted with iodoethane and diazomethane to produce the optically inactive mono-ethyl ester (Ⅵ) and monomethyl ester (Ⅴ) respectively.

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