Construction of 1,2,5‐Tricarbonyl Compounds using Methyl Cyanoacetate as a Glyoxylate Anion Synthon Combined with Copper(I) Iodide‐Catalyzed Aerobic Oxidation

Kim, Se Hee; Kim, Ko Hoon; Kim, Jae Nyoung

doi:10.1002/adsc.201100431

Cited by 32 publications

(18 citation statements)

References 55 publications

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“…Indirect methods for the preparation of the requisite α,δ-diketo esters 5 have been reported by us 10b and others, 36 but the most direct and atom economical approach to these substrates would be a new Stetter reaction between commercial ethyl glyoxylate and α,β-enones. 37 This reaction was previously reported to be unsuccessful with thiazolium carbenes, 36c but we have found that effective catalysis can be realized by employing the Rovis triazolium carbene derived from salt 4 .…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters

et al. 2012

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The dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation has been developed as a technique for the highly stereoselective construction of structurally diverse β-substituted-α-hydroxy carboxylic acid derivatives. Through the development of a privileged m-terphenylsulfonamide for (arene)RuCl(monosulfonamide) complexes with a high affinity for selective α-keto ester reduction, excellent levels of chemo-, diastereo-, and enantiocontrol can be realized in the reduction of β-aryl- and β-chloro-α-keto esters.

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Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters

et al. 2012

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“…Treatment of methyl 3-fluoro-4-nitrobenzoate ( 8 ) with methyl 2-cyanoacetate under basic conditions delivered intermediate 9 . 12 Subsequent copper(I) iodide-catalyzed aerobic oxidation 12 delivered methyl 2-oxo-2-phenylacetate 10 , and from here, target 1a was prepared in parallel to the chemistry employed in Scheme 1. With 1a in hand, saponification and nitro reduction were accomplished as outlined in Scheme 3 to deliver analogs 1b , 1j , and 1k .…”

Section: Resultsmentioning

confidence: 99%

High-Potency Phenylquinoxalinone Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Activators

et al. 2017

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We previously identified phenylquinoxalinone CFTRact-J027 (4) as a cystic fibrosis transmembrane conductance regulator (CFTR) activator with an EC50 of ∼200 nM and demonstrated its therapeutic efficacy in mouse models of constipation. Here, structure v–activity studies were done on 36 synthesized phenylquinoxalinone analogs to identify compounds with improved potency and altered metabolic stability. Synthesis of the phenylquinoxalinone core was generally accomplished by condensation of 1,2-phenylenediamines with substituted phenyloxoacetates. Structure–activity studies established, among other features, the privileged nature of a properly positioned nitro moiety on the 3-aryl group. Synthesized analogs showed improved CFTR activation potency compared to 4 with EC50 down to 21 nM and with greater metabolic stability. CFTR activators have potential therapeutic indications in constipation, dry eye, cholestatic liver diseases, and inflammatory lung disorders.

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“…1 The protocol is a very simple and high-yielding process of 2,5-diketoesters (vide infra, Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Facile Regiocontrolled Three-Step Synthesis of Poly-Substituted Furans, Pyrroles, and Thiophenes: Consecutive Michael Addition of Methyl Cyanoacetate to α,β-Enone, CuI-Mediated Aerobic Oxidation, and Acid-Catalyzed Paal-Knorr Synthesis

Kim¹,

Lim²,

Lim³

et al. 2012

Bulletin of the Korean Chemical Society

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Construction of 1,2,5‐Tricarbonyl Compounds using Methyl Cyanoacetate as a Glyoxylate Anion Synthon Combined with Copper(I) Iodide‐Catalyzed Aerobic Oxidation

Cited by 32 publications

References 55 publications

Asymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters

Asymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters

High-Potency Phenylquinoxalinone Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Activators

Facile Regiocontrolled Three-Step Synthesis of Poly-Substituted Furans, Pyrroles, and Thiophenes: Consecutive Michael Addition of Methyl Cyanoacetate to α,β-Enone, CuI-Mediated Aerobic Oxidation, and Acid-Catalyzed Paal-Knorr Synthesis

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