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Synthesis of α-Methylene-β-Lactams via PPh3-Catalyzed Umpolung Cyclization of Propiolamides

Lin Zhu, Yan Xiong and Chaozhong Li*

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China, Email: cligmail.sioc.ac.cn

L. Zhu, Y. Xiong, C. Li, J. Org. Chem., 2015, 80, 628-633.

DOI: 10.1021/jo502265a (free Supporting Information)


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Abstract

Umpolung enables a facile synthesis of α-methylene-β-lactams. Under the catalysis of triphenylphosphine, a number of 2-propiolamidoacetates or α-propiolamido ketones underwent cyclization to afford the corresponding 4-substituted 3-methyleneazetidin-2-ones in high yields.


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Key Words

β-Lactams, Organocatalysis


ID: J42-Y2015