Methods for the synthesis of α‐keto esters

Kovács, Lajos

doi:10.1002/recl.19931120902

Cited by 27 publications

(13 citation statements)

References 292 publications

(2 reference statements)

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“…In view of both the peculiar structural features and the important biological roles of α-ketoamides, it is not surprising that a plethora of different methods for their efficient synthesis have been and continue to be proposed. However, no comprehensive reviews dealing with the synthesis of α-ketoamides have appeared hitherto in the literature, unlike α-ketoacids − and α-ketoesters. − …”

Section: Introductionmentioning

confidence: 99%

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

2016

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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.

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Section: Introductionmentioning

confidence: 99%

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

2016

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“…2 This unique and versatile functional group provides access to useful building blocks such as α-hydroxy and α-amino esters. 3 Despite positive attributes, the existing reagents and strategies highlighted in Figure 1 are not amenable to widespread adoption of the “glyoxylate anion” tactic in organic synthesis due to case-dependent disadvantages and/or limitations.…”

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confidence: 99%

Asymmetric Synthesis of α-Keto Esters via Cu(II)-Catalyzed Aerobic Deacylation of Acetoacetate Alkylation Products: An Unusually Simple Synthetic Equivalent to the Glyoxylate Anion Synthon

Steward

Johnson

2011

Org. Lett.

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A simple and efficient method for the preparation of β-stereogenic α-keto esters is described using a copper(II)-catalyzed aerobic deacylation of substituted acetoacetate esters. The substrates for the title process arise from catalytic, enantioselective conjugate additions and alkylation reactions of acetoacetate esters. The mild conditions do not induce racemization of the incipient enolizable α-keto ester. The reaction is tolerant of esters, certain ketones, ketals, and nitro groups and utilizes inexpensive, readily available materials.

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“…With the development of synthetic methodology, the cross dehydrogenative coupling reaction has attracted much attention because of the direct construction of C–C and C–X bonds. Thus, although various strategies have been developed for the preparation of α-ketoesters, − , the direct α-ketoesterification via dehydrogenation coupling reaction is still extensively desirable due to the use of simple reactants, shorter reaction steps, and reduced amounts of waste products. However, there have been few reports of α-ketoesterification reaction via direct dehydrogenation coupling of alkyl-substituted aromatics with glyoxylic acid derivatives.…”

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confidence: 99%

Palladium-Catalyzed Direct α-Ketoesterification of 8-Methylquinoline Derivatives with α-Ketoacids via Dehydrogenation Coupling Reaction

Zhang

Deng

et al. 2018

Org. Lett.

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A direct, regiospecific, and efficient palladium-catalyzed α-ketoesterification of 8-methylquinoline derivatives to generate α-ketoesters has been discovered. This reaction is conducted at a mild temperature, free of peroxide, and compatible with air, and various α-ketoesters were achieved with good yields. Importantly, this reaction can be easily amplified to gram level using only 1 mol % of the palladium catalyst, indicating that there is the potential for further reduction of the amount of catalyst loading required for large-scale production.

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Methods for the synthesis of α‐keto esters

Cited by 27 publications

References 292 publications

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

Recent Developments in General Methodologies for the Synthesis of α-Ketoamides

Asymmetric Synthesis of α-Keto Esters via Cu(II)-Catalyzed Aerobic Deacylation of Acetoacetate Alkylation Products: An Unusually Simple Synthetic Equivalent to the Glyoxylate Anion Synthon

Palladium-Catalyzed Direct α-Ketoesterification of 8-Methylquinoline Derivatives with α-Ketoacids via Dehydrogenation Coupling Reaction

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