Recently, the internationally renowned journal Angewandte Chemie International Edition (IF: 16.6) published online the article Experimental and Theoretical Study of Phosphine-Catalyzed Reaction Modes in the Reaction of α-Substituted Allenes with Aryl Imines by Zhou Qingfa's team from the School of Science. Ke Wu, a Class of 2021 Master's candidate, Quanxin Li, an undergraduate student from Shantou University, and Wenbo Su, a Class of 2019 Master's candidate, are the co-first authors of this paper. Professor Zhou Qingfa from CPU and Professor Shaofei Ni from Shantou University are the co-corresponding authors of this paper. China Pharmaceutical University is the first corresponding unit of this paper.
Phosphine-catalyzed reactions have been vigorously developed in the construction of carbon-carbon/carbon-heteroatom bonds, in which the cyclization and cycloaddition reactions of nucleophilic organophosphine-catalyzed bienes and imines have gradually developed into one of the important tools for the construction of carbon rings, heterocyclic compounds and natural products. Itaconamide is a skeletal structure in a variety of natural products, bioactive molecules, and optical materials. By developing a phosphine-catalyzed acyclization reaction, Qingfa Zhou's group has achieved efficient and high stereoselectivity construction of itakamid derivatives under mild conditions. The reaction is different from the classical cyclization reaction mode of hydrene and imine, and undergoes the uncyclization reaction mode of zwitterionic intermediates and arylimides, and the authors have conducted in-depth research on the reaction mechanism, and through a series of control experiments combined with DFT theoretical calculations, it is shown that carbonic acid plays a key role in this reaction mode.
The above work was supported by the National Natural Science Foundation of China (Grant 21572271) and the Talent Research Fund (NTF20022) of Shantou University.
Citations
https://doi.org/10.1002/anie.202314191
