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Nitrenoid from Oxime: A Practical Synthesis of Planar Chiral Ferrocenyl Phenanthridines via Nitrene-Involved Ring-Expansion Reaction |
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| Authors: | Na Li Dr Biqiong Hong Prof Jinbo Zhao Prof Zhenhua Gu |
| Institution: | 1. Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026 P. R. China;2. College of Materials and Chemical Engineering, Minjiang University, Fuzhou, Fujian, 350108 P. R. China;3. Faculty of Chemistry and Life Science, Changchun University of Technology, 2055 Yan'An Street, Changchun, Jilin 130012 P. R. China |
| Abstract: | 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. |
| Keywords: | Nitrenoid Oxime Phenanthridine Planar Chirality Rearrangement |