Stobbe缩合质子化

丁二酸二乙酯及其衍生物和双键化合物在碱性条件下透过重排的加成。【 Perkin加成 】

肽键

丁二酸二乙酯先对双键化合物透过aldol加成，接着演化成酮，强碱拔氢消除酰得到游离。

加成实例

Stobbe重排后游离重排。

Stobbe游离的关环加成。

连续的Stobbe重排。

供参考

1. Stobbe, H. Ber. 1893, 26, 2312. Hans Stobbe (1860-􀀐1938) was born in Tiehenhof, Germany. He earned his Ph.D. In 1889 at the University of Leipzig where he became a professor in 1894.

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编译自： Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Stobbe condensation，page 587-588.