Imidomethylation of C-nucleophiles using O-phthalimidomethyl trichloroacetimidate and catalytic amounts of TMSOTf

Abstract

The O-phthalimidomethyl trichloroacetimidate ( 1 ), as a latent aminomethylating agent, exhibits high electrophilicity towards a variety of C-nucleophiles in the presence of catalytic amounts of TMSOTf and mild reaction conditions. The nucleophiles include aromatics, alkenes and active methylene compounds 2– 11 whereby a phthalimidomethyl group could be introduced to give compounds 12– 22 . Removal of the phthaloyl group gave the respective amines, β-amino ketones, and β-amino acids. The O-(trichloroacetamido)methyl trichloroacetimidate ( 35 ) was also found to be a good amidomethylating agent.