60026-17-7Relevant academic research and scientific papers
Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
Kaiser, Daniel,Teskey, Christopher J.,Adler, Pauline,Maulide, Nuno
supporting information, p. 16040 - 16043 (2017/11/22)
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.
Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides
De La Torre, Aurélien,Kaiser, Daniel,Maulide, Nuno
supporting information, p. 6578 - 6581 (2017/05/29)
A suite of flexible and chemoselective methods for the transition-metal-free oxidation of amides to α-keto amides and α-hydroxy amides is presented. These highly valuable motifs are accessed in good to excellent yields and stereoselectivities with high functional group tolerance. The utility of the method is showcased by the formal synthesis of a potent histone deacetylase inhibitor.
Chemoselective intermolecular α-arylation of amides
Peng, Bo,Geerdink, Danny,Fares, Christophe,Maulide, Nuno
supporting information, p. 5462 - 5466 (2014/06/09)
A new approach for the fully chemoselective α-arylation of amides is presented. By means of electrophilic amide activation, aryl groups can be regioselectively introduced α- to amides, even in the presence of esters and alkyl ketones. Mechanistic studies reveal key reaction intermediates and emphasize a remarkably subtle base effect in this transformation. Arylating me softly: A new approach for the fully chemoselective α-arylation of amides has been developed. When electrophilic amide activation is employed, aryl groups can be regioselectively introduced in the position α to the amide, and that even in the presence of esters or alkyl ketones. Mechanistic studies emphasize a remarkably subtle base effect in this transformation.
Catalytic hydrogenation of amides to amines under mild conditions
Stein, Mario,Breit, Bernhard
supporting information, p. 2231 - 2234 (2013/03/28)
Under (not so much) pressure: A general method for the hydrogenation of tertiary and secondary amides to amines with excellent selectivity using a bimetallic Pd-Re catalyst has been developed. The reaction proceeds under low pressure and comparatively low temperature. This method provides organic chemists with a simple and reliable tool for the synthesis of amines. Copyright
Gold-catalyzed amide synthesis from aldehydes and amines in aqueous medium
Li, Gai-Li,Kung, Karen Ka-Yan,Wong, Man-Kin
supporting information; experimental part, p. 4112 - 4114 (2012/06/16)
An efficient gold-catalyzed amide synthesis from aldehydes and amines in aqueous medium under mild reaction conditions has been developed.
A new efficient synthesis of α-methyl-β-ketoesters through an Eschenmoser sulfide reaction
Bellec, Christian,Gaurat, Olivier
, p. 1289 - 1293 (2007/10/03)
Various α-methyl-β-ketoesters were readily synthesized through Eschenmoser condensation of thioamides with a commercially available bromoester. β-Enaminoesters were easily prepared through this sulfide contraction reaction and were hydrolysed to afford the corresponding β-ketoesters in moderate to good yields.
