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Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
Article de revue   Avec comité de lecture

Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides

Daniel Kaiser, Christopher J. Teskey, Pauline Adler et Nuno Maulide
Journal of the American Chemical Society, Vol.139(45), pp.16040-16043
15/11/2017
PMID: 29099184

Résumé

Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology
A new approach for the synthesis of 1,4-dicarbonyl compounds is reported. Chemoselective activation of amide carbonyl functionality and subsequent umpolung via N-oxide addition generates an electrophilic enolonium species that can be coupled with a wide range of nucleophilic enolates. The method conveys broad functional group tolerance on both components, does not suffer from formation of homocoupling byproducts and avoids the use of transition metal catalysts.

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