title: Recent Developments in General Methodologies for the Synthesis of α-Ketoamides.
abstract: The α-ketoamide motif is widely found in many natural products and drug candidates with relevant biological activities. Furthermore, α-ketoamides are attractive candidates to synthetic chemists due to the ability of the motif to access a wide range of functional group transformations, including multiple bond-forming processes. For these reasons, a vast array of synthetic procedures for the preparation of α-ketoamides have been developed over the past decades, and the search for expeditious and efficient protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged since the 1990s up to the present. The different synthetic routes have been grouped according to the way the α-ketoamide moiety has been created. Thus, syntheses of α-ketoamides proceeding via C(2)-oxidation of amide starting compounds are detailed, as are amidation approaches installing the α-ketoamide residue through C(1)-N bond formation. Also discussed are the methodologies centered on C(1)-C(2) σ-bond construction and C(2)-R/Ar bond-forming processes. Finally, the literature regarding the synthesis of α-ketoamide compounds by palladium-catalyzed double-carbonylative amination reactions is discussed.
authors.affiliation: Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara , Via Fossato di Mortara 17, 44121 Ferrara, Italy.
authors.forename: Carmela
authors.initials: C
authors.lastname: De Risi
authors.affiliation: Istituto Universitario di Studi Superiori "IUSS-Ferrara 1391", Via delle Scienze 41/b, 44121 Ferrara, Italy.
authors.forename: Gian Piero
authors.initials: GP
authors.lastname: Pollini
authors.affiliation: Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara , Via Fossato di Mortara 17, 44121 Ferrara, Italy.
authors.forename: Vinicio
authors.initials: V
authors.lastname: Zanirato
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D000588:Amines / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000639:trends*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: D000577:Amides; D000588:Amines; D007659:Ketones