Abstract
The reaction of allylic amines with dimethyl acetylenedicarboxylate is subject to protic acid catalysis and affords 15, the product of Michael addition and aza-Claisen rearrangement. The sequence involves Michael addition of 4c or 19-21 to generate an intermediateN-alkenyl ammonium salt 14 that undergoes a charge-accelerated rearrangement to 15. Toluenesulfonic acid is a useful catalyst for the Mickael addition step. Benzoic acid is not effective because the intermediate 14 is competitively dealkylated by the benzoate counterion. In one case, the intermediate N-alkenylammonium ion 18 has been detected by 1 H NMR spectroscopy and has been observed to undergo the aza-Claisen rearrangement at -20 o C
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