Synthesis of racemic δ,δ-dimethylproline derivatives
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 prol...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2013 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/111481 |
| Acceso en línea: | http://hdl.handle.net/10261/111481 |
| Access Level: | acceso abierto |
| Palabra clave: | Synthetic methods Proline analogues Nitrogen heterocycles Regioselectivity Amino acids |
| Sumario: | 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. |
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