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Preference of β-Lactam Formation in Cu(I)-Catalyzed Intramolecular Coupling of Amides with Vinyl Bromides
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Chinese Academy of Sciences.
, ‡University of Science and Technology of China.
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. Tandem C−N bond formation was then successfully developed to allow the convenient generation of medium-sized lactams.
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History
- Published In Issue September 18, 2008
- Article ASAPAugust 23, 2008
- Received: July 09, 2008
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