Homologation of α-aryl amino acids through quinone-catalyzed decarboxylation/Mukaiyama-Mannich addition.
| Autor: | Haugeberg BJ; Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA. mclift@ku.edu., Phan JH; Eli Lilly and Company, 893 S. Delaware Street, DC - 1920, Indianapolis, IN 46285, USA., Liu X; Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA. mclift@ku.edu., O'Connor TJ; Department of Chemistry, University of California - Berkeley, 419 Latimer Hall, CA 94720-1460, USA., Clift MD; Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA. mclift@ku.edu. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2017 Mar 09; Vol. 53 (21), pp. 3062-3065. |
| DOI: | 10.1039/c7cc00485k |
| Abstrakt: | A new method for amino acid homologation by way of formal C-C bond functionalization is reported. This method utilizes a 2-step/1-pot protocol to convert α-amino acids to their corresponding N-protected β-amino esters through quinone-catalyzed oxidative decarboxylation/in situ Mukaiyama-Mannich addition. The scope and limitations of this chemistry are presented. This methodology provides an alternative to the classical Arndt-Eistert homologation for accessing β-amino acid derivatives. The resulting N-protected amine products can be easily deprotected to afford the corresponding free amines. |
| Databáze: | MEDLINE |
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