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N-Acyliminium ion cyclizations were studied with allenylmethylsilanes to synthesize nitrogen heterocycles. N-Acyliminium ion cyclizations were carried out by exposure of precursors 6 and 7 to Lewis acid. The precursors 6 were converted to pyrrolizidinone derivatives 9 with an exo-allene moiety, while the precursors 7 to indolizidinone derivatives 10 with an exo-1,3-diene moiety.
The intramolecular titanium-mediated coupling reaction of α-substituted succinimides and mono-substituted olefins took place with complete regiocontrol, but without diastereoselectivity. The corresponding intermolecular coupling exhibited lack of regio- and diastereocontrol. Also included were stereochemical studies of catalytic hydrogenation and NaBH3CN reduction of the cyclization products.
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