Tetrahedron

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

IAI Ali, H El Sayed, RR Schmidt

Index: Ali, Ibrahim A. I.; El Ashry, El Sayed H.; Schmidt, Richard R. Tetrahedron, 2004 , vol. 60, # 22 p. 4773 - 4780

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Citation Number: 20

Abstract

The O-phthalimidomethyl trichloroacetimidate (), 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 whereby a phthalimidomethyl group could be introduced to give compounds. Removal of the phthaloyl group gave the respective ...