%0 Generic %A Charette, André B. %A Mathieu, Simon %A Martel, Jonathan %D 2005 %T Electrophilic Activation of Lactams with Tf2O and Pyridine:  Expedient Synthesis of (±)-Tetraponerine T4 %U https://acs.figshare.com/articles/dataset/Electrophilic_Activation_of_Lactams_with_Tf_sub_2_sub_O_and_Pyridine_Expedient_Synthesis_of_Tetraponerine_T4/3255481 %R 10.1021/ol052069n.s002 %2 https://ndownloader.figshare.com/files/5090860 %K building blocks %K nucleophilic addition %K presence %K Tf 2 O %K triflic anhydride %K electrophilic activation %K dihydropyridine %K synthesis %K Tetraponerine %K Pyridine %K pyrrolidone %K Lactam %K organometallic reagents %K pyridinium imidate %K pyridine %K Expedient %K lactam %K Electrophilic Activation %K NMR %K formation %K Synthesi %K tetraponerine %X 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). %I ACS Publications