The chair/boat topology of the amide-acetal Claisen rearrangement transition state has been studied for cyclic N-alkyl amide acetals of 5, 6, and 7 membered rings. The topology of the chair or boat transition states can be determined from the syn/anti ratio of the reaction. The ring size of the cyclic amide acetals has a significant effect on the selectivity. All products were characterized by 1H and 13C NMR, GC-MS, and IR.

Amide-acetal Claisen rearrangements with acetals of cyclic amides

243rd National Meeting (2012)

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