Organic Chemistry Portal

Abstracts

Search:

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

Dandan Zuo, Tao Zhang, 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

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

DOI: 10.1021/acs.orglett.2c01739


see article for more reactions

Abstract

In palladium-catalyzed regioselective [5 + 1] annulation reactions of vinyl aziridines/epoxides with ClCF2COONa, vinyl aziridines/epoxides act as heteroatom-containing five-atom synthons, and commercially available and cheap ClCF2COONa is the carbonyl source. This protocol efficiently provides δ-lactams and δ-lactones in good yields.


see article for more examples


proposed mechanism



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

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


Key Words

5,6-dihydro-2-pyridinones


ID: J54-Y2022