ol052069n_si_002.cif (38.88 kB)
Electrophilic Activation of Lactams with Tf2O and Pyridine: Expedient Synthesis of (±)-Tetraponerine T4
dataset
posted on 2005-11-24, 00:00 authored by André B. Charette, Simon Mathieu, Jonathan MartelThe 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).