Imidomethylation of C-nucleophiles using O-phthalimidomethyl trichloroacetimidate and catalytic amounts of TMSOTf |
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| Authors: | Ibrahim AI Ali Richard R Schmidt |
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| Institution: | a Department of Chemistry, University of Konstanz, Fach M 725, D-78457 Konstanz, Germany
b Department of Chemistry, Faculty of Science, University of Alexandria, Alexandria, Egypt |
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| 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. |
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| Keywords: | O-Phthalimidomethyl trichloroacetimidate Imidomethylation Amidomethylation Amino ketones Amino acids |
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