The synthesis of cyclopropyl amines and cyclopropanols by the reaction of enamines and trimethylsilyl enol ethers with CH2I2 and Et3Al

The reaction of enamines with 2 equiv of Et3Al and CH2I2 at room temperature in CH2Cl2 results in the formation of cyclopropyl amines in high yields (68-89%). Substituted 1-phenylcyclopropan-1-ols were also synthesized from trimethylsilyl enol ethers. The paper demonstrates the advantage of using aluminum carbenoids over traditional cyclopropanation reagents (diazomethane, Simmons-Smith and Furukawa reagents) for the preparation of cyclopropyl amines.