Highly Stereoselective and Practical Synthesis of a-Trichloromethyl Amines and 2,2-Dichloroaziridines from Chloroform

A highly stereoselective and practical synthesis of a-trichloromethyl amines by nucleophilic trichloromethylation of N-(tert-butylsulfinyl)imines with chloroform was achieved. The obtained a-trichloromethyl amines can be further transformed into chiral 2,2-dichloroaziridines through an intramolecular nucleophilic substitution methodology. 2,2-Dichloroaziridines can also be produced directly from chloroform and N-(tert-butylsulfinyl)imines through a one-pot procedure.