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Kaiser D, Teskey CJ, Adler P, et al. Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides. J Am Chem Soc. 2017;139(45):16040-16043doi: 10.1021/jacs.7b08813.
Kaiser, D., Teskey, C. J., Adler, P., & Maulide, N. (2017). Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides. Journal of the American Chemical Society, 139(45), 16040-16043. https://doi.org/10.1021/jacs.7b08813
Kaiser, Daniel, et al. "Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides." Journal of the American Chemical Society vol. 139,45 (2017): 16040-16043. doi: https://doi.org/10.1021/jacs.7b08813
Kaiser D, Teskey CJ, Adler P, Maulide N. Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides. J Am Chem Soc. 2017 Nov 15;139(45):16040-16043. doi: 10.1021/jacs.7b08813. Epub 2017 Nov 03. PMID: 29099184; PMCID: PMC5691317.
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J Am Chem Soc. 2017 Nov 15;139(45):16040-16043. doi: 10.1021/jacs.7b08813. Epub 2017 Nov 03.

Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides.

Journal of the American Chemical Society

Daniel Kaiser, Christopher J Teskey, Pauline Adler, Nuno Maulide

Affiliations

  1. Institute of Organic Chemistry, University of Vienna , Währinger Strasse 1090, Vienna, Austria.

PMID: 29099184 PMCID: PMC5691317 DOI: 10.1021/jacs.7b08813

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.

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