The lactam synthon 2-azabicyclo[2.2.1]hept-5-en-3-one was converted into its enantiomer by a 5-step sequence incorporating a skeletal rearrangement mediated by anchimeric assistance of the nitrogen atom; the route proceeded via a tosylate intermediate prone to racemization.
C. F. Palmer and R. McCague, J. Chem. Soc., Perkin Trans. 1, 1995, 1201 DOI: 10.1039/P19950001201
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