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Literature DB >> 28485589

Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides.

Aurélien de la Torre¹, Daniel Kaiser¹, Nuno Maulide¹.

Abstract

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.

Entities: Chemical

Year: 2017 PMID： 28485589 DOI： 10.1021/jacs.7b02983

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

16 in total

1. Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.

Authors: Giovanni Di Mauro; Boris Maryasin; Daniel Kaiser; Saad Shaaban; Leticia González; Nuno Maulide
Journal: Org Lett Date: 2017-07-13 Impact factor: 6.005

2. Interception of 1,2-cyclohexadiene with TEMPO radical.

Authors: Matthew S McVeigh; Neil K Garg
Journal: Tetrahedron Lett Date: 2021-11-15 Impact factor: 2.415

3. Uniting Amide Synthesis and Activation by P^III/P^V-Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines.

Authors: Jeffrey M Lipshultz; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2021-09-03 Impact factor: 16.383

Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides.

1. Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.

2. Interception of 1,2-cyclohexadiene with TEMPO radical.

3. Uniting Amide Synthesis and Activation by P^III/P^V-Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines.

4. Hydrative Aminoxylation of Ynamides: One Reaction, Two Mechanisms.

5. Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates.

6. Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides.

7. Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones.

8. Differentiation between enamines and tautomerizable imines in the oxidation reaction with TEMPO.

9. Highly selective transition-metal-free transamidation of amides and amidation of esters at room temperature.

10. Direct Synthesis of Enamides via Electrophilic Activation of Amides.