Synthesis of beta,gamma-unsaturated lactams via a magnesium iodide promoted ring expansion of secondary methylenecyclopropyl amides.
A novel and efficient route to exo-beta,gamma-unsaturated lactams from substituted and non-substituted secondary methylenecyclopropyl amides is reported. Subsequent modification of the resulting exo-beta,gamma-unsaturated lactams provides access to several pharmaceutically relevant scaffolds. [reaction: see text].
Scott
Mark E
ME
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Schwarz
Christina A
CA
Lautens
Mark
M
D000577:Amides / Q000737:chemistry*; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis*; D017616:Magnesium Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy
D000577:Amides; D003521:Cyclopropanes; D007454:Iodides; D007769:Lactams; D017616:Magnesium Compounds; C510205:magnesium iodide