Bicyclic lactams 14–17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3: 1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that the indenes 19 and 21 are formed preferentially with retention of configuration at the spiro carbon atom and the naphthalenes 20 and 22 with inversion.
A. A. Bahajaj, P. D. Bailey, M. H. Moore, K. M. Morgan and J. M. Vernon, J. Chem. Soc., Chem. Commun., 1994, 2511 DOI: 10.1039/C39940002511
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