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Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones

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An unexpected C-C bond cleavage was observed in trichloroacetamide-tethered ketones under amine treatment and exploited to develop a new synthesis of normophans from 4-amidocyclohexanones. The reaction involves an unprecedented intramolecular haloform-type reaction of trichloroacetamides promoted by enamines (generated in situ from ketones) as counter-reagents. The methodology was applied to the synthesis of compounds embodying the 6-azabicyclo[3.2.1]octane framework.

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DIABA, Faïza, et al. Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones. Organic Letters. 2015. Vol. 2015, num. 17, pags. 3860-3863. ISSN 1523-7060. [consulted: 28 of June of 2026]. Available at: https://hdl.handle.net/2445/128365

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