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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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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

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Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones