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

Qiwu Zhao and Chaozhong Li*

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

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

DOI: 10.1021/ol801545a (free Supporting Information)


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Abstract

A general and highly efficient synthesis of 4-alkylidene-2-azetidinones was achieved by the Cu(I)-catalyzed intramolecular C-N coupling of amides with vinyl bromides. This 4-exo ring closure was found to be fundamentally preferred over other modes (5-exo, 6-exo, and 6-endo) of cyclization under copper catalysis.

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

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

Preference of 4-exo Ring Closure in Copper-Catalyzed Intramolecular Coupling of Vinyl Bromides with Alcohols

Y. Fang, C. Li, J. Am. Chem. Soc., 2007, 129, 8092-8093.


Key Words

β-Lactams, Ullmann Synthesis


ID: J54-Y2008-2600