The bis(homoallylic) stabilisation of an acyliminium ion and reactions with nucleophiles

Article abstract of DOI:10.1016/S0040-4039(98)00486-9

The bis(alkylation) of N-benzylhomophthalimide by allyl bromide in the presence of aqueous ethanolic sodium hydroxide and regioselective reduction gave the bis(homoallylic) stabilised acyliminium ion precursor and hence the ion that was studied by ¹³C nmr spectroscopy: the subsequent fate of the ion, in a number of cases leading to the formation of a new five-membered ring, was shown to depend on the Lewis acid used to generate the ion and on the nucleophiles that were present in the reaction medium.