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Título: | Stereoselective multigram-scale synthesis of cis- and trans-β- phenylproline derivatives |
Autor: | Rodríguez-Díaz, Isabel CSIC; Calaza, M. Isabel CSIC; Jiménez, Ana I. CSIC ORCID; Cativiela, Carlos CSIC ORCID | Fecha de publicación: | 2012 | Editor: | Elsevier | Citación: | Tetrahedron 68(47): 9578-9582 (2012) | Resumen: | Efficient routes for the gram-scale preparation of the proline analogues that bear a phenyl substituent attached to the pyrrolidine β carbon (cis- and trans-β-phenylproline) have been developed. The cis derivative was synthesized from N-Boc-β-alanine in six steps and 78% overall yield. The generation of a vinyl triflate with full regiochemical control together with a high-yielding cross-coupling reaction and a completely stereoselective hydrogenation are at the basis of the high efficiency of the procedure. Epimerization of the cis β-phenylproline derivative with lithium bis(trimethylsilyl)amide provided access to the trans isomer. © 2012 Elsevier Ltd. All rights reserved. | URI: | http://hdl.handle.net/10261/65110 | DOI: | 10.1016/j.tet.2012.09.069 | Identificadores: | doi: 10.1016/j.tet.2012.09.069 issn: 0040-4020 |
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