Novel Oxidative Generation of Ammonium Ylides and the Subsequent Silicon Polonovski Reaction
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We have demonstrated a novel oxidative generation of ammonium ylides by employing allylic amines having a silyl group. Treatment of <I>N</I>-(α-silylmethyl)-<I>N</I>-allylic amines with an oxidant, followed by acetic anhydride, brought about a tandem Brook rearrangement/silicon Polonovski reaction via the generation of ammonium ylides to give the corresponding amides, whereas the reaction of <I>N</I>-(α-cyano-α-silylmethyl)-<I>N</I>-allylic amines with an oxidant afforded the corresponding formamides.
- Chemistry Letters
Chemistry Letters 37(4), 442-443, 2008-04-05
The Chemical Society of Japan