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The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes

Jian-Jun Feng, Tao-Yan Lin, Chao-Ze Zhu, Huamin Wang, Hai-Hong Wu and Junliang Zhang*

*Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, P. R. China, Email:

J.-J. Feng, T.-Y. Lin, C.-Z. Zhu, H. Wang, H.-H. Wu, J. Zhang, J. Am. Chem. Soc., 2016, 138, 2178-2181.

DOI: 10.1021/jacs.6b00386

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By using [Rh(NBD)2]BF4 as the catalyst for intermolecular cycloaddition of vinylaziridines with alkynes, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. When the catalyst was changed to [Rh(η6-C10H8) (COD)]SbF6, the alternative [5 + 2] cycloadducts were selectively formed under otherwise identical conditions.

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ID: J48-Y2016