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Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones

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https://figshare.com/articles/dataset/Synthesis_of_Normorphans_through_an_Efficient_Intramolecular_Carbamoylation_of_Ketones/2143120
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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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2016-02-13
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