Nitrenoid from Oxime: A Practical Synthesis of Planar Chiral Ferrocenyl Phenanthridines via Nitrene-Involved Ring-Expansion Reaction
Nitrenoid from Oxime: A Practical Synthesis of Planar Chiral Ferrocenyl Phenanthridines via Nitrene-Involved Ring-Expansion Reaction
复制标题
肟中的氮烯基：通过氮烯-涉及环-膨胀反应实际合成平面手性二茂铁基菲啶
DOI：
10.1002/anie.202215530
复制
发表时间：
2022-11-29
影响因子：
16.6
通讯作者：
Gu, Zhenhua
中科院分区：
文献类型：
--
作者：
Li, Na;Hong, Biqiong;Gu, Zhenhua
氮烯和类氮烯是一类反应活性很高的化合物，是合成含氮杂环化合物的关键中间体。本工作以镁配位的类氮杂环化合物的扩环反应为关键步骤，发展了肟类化合物与格氏试剂（含或不含二乙基锌）反应合成菲啶类化合物的实用方法。该方法已用于合成光学活性的平面手性二茂铁基菲啶。
Nitrenes and nitrenoids are highly reactive species and the proposed key intermediates in nitrogen-containing heterocyclic compound synthesis. In this work, we developed a practical method for the synthesis of phenanthridines by the reaction of oximes and Grignard reagents (with or without diethylzinc) via ring-expansion of magnesium coordinated nitrenoid complex as the key step. The method has been used to synthesize optically active planar chiral ferrocenyl phenanthridines.