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Electrophilic Activation of Lactams with Tf2O and Pyridine:  Expedient Synthesis of (±)-Tetraponerine T4

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posted on 24.11.2005, 00:00 by André B. Charette, Simon Mathieu, Jonathan Martel
The electrophilic activation of lactams with triflic anhydride in the presence of pyridine was investigated by NMR. It was found that 2-pyrrolidone led to the clean formation of the corresponding pyridinium imidate in 89% isolated yield. The subsequent nucleophilic addition of organometallic reagents led to 2-substituted dihydropyridines. A synthesis of (±)-tetraponerine T4 with three simple building blocks was accomplished in 3 steps (38% yield).