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

Abstract

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.