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  • Title: Preference of beta-lactam formation in Cu(I)-catalyzed intramolecular coupling of amides with vinyl bromides.
    Author: Zhao Q, Li C.
    Journal: Org Lett; 2008 Sep 18; 10(18):4037-40. PubMed ID: 18722451.
    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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