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Título: | Synthesis of racemic δ,δ-dimethylproline derivatives |
Autor: | Rodríguez-Díaz, Isabel CSIC; Calaza, M. Isabel CSIC; Cativiela, Carlos CSIC ORCID | Palabras clave: | Synthetic methods Proline analogues Nitrogen heterocycles Regioselectivity Amino acids |
Fecha de publicación: | 2013 | Editor: | Wiley-VCH | Citación: | European Journal of Organic Chemistry 6: 1093-1099 (2013) | Resumen: | A versatile methodology for the preparation of racemic δ,δ- dimethylproline derivatives has been developed. Methyl N-Boc-δ,δ- dimethylprolinate was synthesized from a β-amino acid in six steps and 55 % overall yield. The route is amenable to the preparation of a broad range of δ,δ-disubstituted prolines by starting with the adequate β-amino acids. In addition, one of the intermediate compounds in the synthetic route has been used for the preparation of a δ,δ- dimethylproline derivative that is substituted at the β-position with a phenyl group. This has been achieved by coupling phenylboronic acid with a regioselectively generated vinyl triflate followed by a stereoselective hydrogenation. δ,δ-Dimethylproline derivatives have been efficiently synthesized by employing a β-amino acid as the starting material. The methodology is amenable to the preparation of other δ,δ- disubstituted prolines. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | Versión del editor: | https://doi.org/10.1002/ejoc.201201420 | URI: | http://hdl.handle.net/10261/111481 | DOI: | 10.1002/ejoc.201201420 | Identificadores: | doi: 10.1002/ejoc.201201420 issn: 1434-193X e-issn: 1099-0690 |
Aparece en las colecciones: | (ISQCH) Artículos |
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EJOCracemic.pdf | 289,52 kB | Adobe PDF | Visualizar/Abrir |
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