Palladium-Catalyzed Carbonylative [5+1] Cycloaddition of N-Tosyl Vinylaziridines: Solvent-Controlled Divergent Synthesis of α,β- and β,γ-Unsaturated δ-Lactams

Tao Zhang, Shichong Wang, Dandan Zuo, Jingjing Zhao*, Wen Luo*, Chaojie Wang and Pan Li*

*Key Laboratory of Natural Medicine and Immuno-Engineering, Henan University, Kaifeng 475004, P. R. China, Email: zhaojingjinghenu.edu.cn, luowen83163.com, panlihenu.edu.cn

T. Zhang, S. Wang, D. Zuo, J. Zhao, W. Luo, C. Wang, P. Li, J. Org. Chem., 2022, 87, 10372-10376.

DOI: 10.1021/acs.joc.2c00710

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Abstract

A palladium-catalyzed carbonylative [5+1] cycloaddition of N-tosyl vinylaziridines with CO provides α,β-unsaturated δ-lactams in dimethylformamide and β,γ-unsaturated δ-lactams in tetrahydrofuran in very good yields.

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proposed mechanism

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Palladium-Catalyzed Regioselective [5 + 1] Annulation of Vinyl Aziridines/Epoxides with ClCF₂COONa

D. Zuo, T. Zhang, J. Zhao, W. Luo, C. Wang, P. Li, Org. Lett., 2022, 24, 4630-4634.

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Key Words

α,β-unsaturated δ-lactams, β,γ-unsaturated δ-lactams

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ID: J42-Y2022