General and Highly Efficient Synthesis of 2-Alkylideneazetidines and β-Lactams via Copper-Catalyzed Intramolecular N-Vinylation

Hongjian Lu and Chaozhong Li*

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, PRC, Email: cligmail.sioc.ac.cn

H. Lu, C. Li, Org. Lett., 2006, 8, 5365-5367.

DOI: 10.1021/ol062274i

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Abstract

N-Tosyl-3-halo-3-butenylamines underwent efficient Ullmann-type coupling to afford 2-alkylideneazetidines, which could be readily converted to the corresponding β-lactams by oxidation with O₃.

see article for more examples

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Preference of β-Lactam Formation in Cu(I)-Catalyzed Intramolecular Coupling of Amides with Vinyl Bromides

Q. Zhao, C. Li, Org. Lett., 2008, 10, 4037-4040.

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Key Words

Ullmann Coupling, Ozonolysis, Ozone, Azetidines, β-Lactams

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ID: J54-Y2006-3680