Transition metal-catalyzed cycloaddition of cyclopropane with alkyne is one of the most important methods for the construction of 5-membered carbon ring motifs. However, the reaction substrate has been limited into activated cyclopropane derivatives, such as highly strained cyclopropanes (cyclopropene and alkylidenecyclopropane), D-A cyclopropanes, vinylcyclopropanes and cyclopropyl ketones or imines for a long time. Readily-available and easily-transformable cyclopropyl carboxylates remains an elusive challenge in this reaction. Until recently, Mengchun Ye group in College of Chemistry in Nankai University achieved a breakthrough in this regard bu using a secondary phosphine oxide (SPO)-assisted bimetallic catalysis, in which the complex SPO-Ni-Al not only activated the substrate but also directed the oxidative addition of nickel with C–C bond. Based on the method, a series of cycloaddition products were obtained in up to 99% yield and 94% ee.

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Qi-Sheng Liu, De-Yin Wang, Zhi-Jun Yang, Yu-Xin Luan, Jin-Fei Yang, Jiang-Fei Li, You-Ge Pu, and Mengchun Ye* Ni−Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne. J. Am. Chem. Soc. 2017, 139, 18150～18153.