Fast Pd- and Pd/Cu-Catalyzed Direct C–H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters
| Autor: | Emilien Demory, Benoit Baptiste, Pierre Y. Chavant, Véronique Blandin, Daniel Farran |
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| Přispěvatelé: | Département de Chimie Moléculaire - Synthèse Et Réactivité en Chimie Organique (DCM - SeRCO), Département de Chimie Moléculaire (DCM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Joseph Fourier - Grenoble 1 (UJF)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Joseph Fourier - Grenoble 1 (UJF), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Joseph Fourier - Grenoble 1 (UJF) |
| Rok vydání: | 2012 |
| Předmět: |
chemistry.chemical_classification
Pivalic acid Amino esters [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Chemistry Aryl Organic Chemistry Halide 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Nitrone Catalysis chemistry.chemical_compound Enantiopure drug Copper bromide Organic chemistry |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2012, 77 (18), pp.7901-12. ⟨10.1021/jo301114k⟩ |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo301114k |
| Popis: | International audience; Cocatalysis by pivalic acid or copper bromide allows a very fast, clean, and high-yielding palladium-catalyzed coupling of a large array of aryl, thienyl, and pyridyl halides with cyclic nitrones, including DMPO. The study of the reaction conditions, scope, and mechanism is presented. Applied to the chiral nitrone MiPNO, this transformation provides a straightforward access to enantiopure α-methyl α-arylglycine esters. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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