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Article

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Accepted version

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2015-01-21

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/128365

Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones

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https://doi.org/10.1021/acs.orglett.5b01832

Abstract

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.

Subject

Cetones, Amines, Síntesi orgànica, Reaccions químiques

Subject (English)

Ketones, Amines, Organic synthesis, Chemical reactions

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

Citation

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: 9 of August of 2026]. Available at: https://hdl.handle.net/2445/128365

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