Potassium carbonate-promoted stereospecific 5-endo-trig cyclization of unactivated allenes in the absence of any transition metals.
Potassium carbonate-promoted stereospecific 5-endo-trig cyclization of unactivated allenes in the absence of any transition metals.
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DOI：
10.1021/ol053094w
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发表时间：
2006-02
期刊：
影响因子：
5.2
通讯作者：
H. Ohno;Y. Kadoh;N. Fujii;Tetsuaki Tanaka
中科院分区：
文献类型：
--
作者：
H. Ohno;Y. Kadoh;N. Fujii;Tetsuaki Tanaka
本文描述了在碱性条件下由带有保护氨基的简单未活化的联烯形成3-吡咯啉的反应。α-氨基联烯与碳酸钾在DMF中回流处理，在没有任何过渡金属催化剂的情况下，通过5-内-内模式环化异构化以良好至优异的产率得到相应的3-吡咯啉。具有轴向手性的内联烯反应以立体选择性的方式得到相应的3-吡咯啉。
Formation of 3-pyrrolines from simple unactivated allenes bearing a protected amino group under basic conditions is described. Treatment of alpha-amino allenes with potassium carbonate in DMF under reflux in the absence of any transition-metal catalysts gave the corresponding 3-pyrrolines in good to excellent yields, by 5-endo-trig mode cycloisomerization. The reaction of internal allenes with an axial chirality afforded the corresponding 3-pyrrolines in a stereoselective manner.