Synthesis of unsaturated seven-membered ring lactams through palladium-catalyzed amination and intramolecular cyclocarbonylation reactions of amines and Baylis-Hillman acetates.
A versatile synthesis of unsaturated seven-membered ring lactams has been developed. The sequence involves hydroamination of Baylis-Hillman acetate with amines, followed by intramolecular cyclocarbonylation reactions of the resulting allylamines. This process can tolerate a wide array of functional groups, and affords lactams in excellent yields.
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
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D000085:Acetates / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000737:chemistry*; D001596:Benzylamines / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D000085:Acetates; D000588:Amines; D001596:Benzylamines; D007769:Lactams; D010165:Palladium; D002244:Carbon; C030796:benzylamine