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Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones Diaba, Faïza Montiel Achong, Juan Andrés Serban, Georgeta Bonjoch i Sesé, Josep Cetones Amines Síntesi orgànica Reaccions químiques Ketones Amines Organic synthesis Chemical reactions 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. 2019-02-18T10:49:20Z 2019-02-18T10:49:20Z 2015-01-21 2019-02-18T10:49:20Z info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 1523-7060 https://hdl.handle.net/2445/128365 654621 26197207 eng Versió postprint del document publicat a: https://doi.org/10.1021/acs.orglett.5b01832 Organic Letters, 2015, vol. 2015, num. 17, p. 3860-3863 https://doi.org/10.1021/acs.orglett.5b01832 (c) American Chemical Society , 2015 info:eu-repo/semantics/openAccess 4 p. application/pdf American Chemical Society Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)