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Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides

Author:
Kaiser, Daniel, Teskey, Christopher J., Adler, Pauline, Maulide, Nuno
Source:
Journal of the American Chemical Society 2017 v.139 no.45 pp. 16040-16043
ISSN:
1520-5126
Subject:
Lewis acids, Lewis bases, amides, byproducts, catalysts, chemoselectivity, moieties
Abstract:
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.
Agid:
5860364