Electrophilic Activation of Lactams with Tf2O and Pyridine: Expedient Synthesis of (±)-Tetraponerine T4
2005-11-24T00:00:00Z (GMT) by
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).
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