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Aryne‐Induced Novel Tandem 1,2‐Addition/(3+2) Cycloaddition to Generate Imidazolidines and Pyrrolidines
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2015-07-03 , DOI: 10.1002/anie.201503319
Sharada P. Swain , Yi-Chun Shih , Shwu-Chen Tsay , Joby Jacob , Chun-Cheng Lin , Kuo Chu Hwang , Jia-Cherng Horng , Jih Ru Hwu

A new “single‐flask” method was developed for the synthesis of imidazolidines and pyrrolidines with high stereoselectivity. First, a Schiff base was arylated with an aryne. Second, an intramolecular proton transfer took place from the methylene position to the anionic aryne ring. Third, the resultant ylide reacted with a second equivalent of the same Schiff base in situ or an electron‐deficient alkene through a (3+2) cycloaddition. These sequential tandem 1,2‐addition/(3+2) cycloaddition reactions led to the desired heterocycles in 63–88 % yields.

中文翻译:

Aryne诱导的新型串联1,2-加成/(3 + 2)环加成反应生成咪唑烷和吡咯烷

开发了一种新的“单烧瓶”方法,用于合成具有高立体选择性的咪唑烷和吡咯烷。首先,将席夫碱与芳烃芳基化。第二,分子内质子从亚甲基位置发生转移至阴离子芳烃环。第三,生成的叶立德通过(3 + 2)环加成反应与第二当量的相同席夫碱原位反应或电子不足的烯烃发生反应。这些顺序的串联1,2-加成/(3 + 2)环加成反应以63-88%的产率产生了所需的杂环。
更新日期:2015-07-03
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