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Título: | Efficient stereodivergent synthesis of cis-(2R,4S)- and trans-(2R,4R)-4-phosphonomethyl-2-piperidinecarboxylic acids from the same chiral imine derived from (R)-glyceraldehyde |
Autor: | Etayo, Pablo CSIC; Badorrey, Ramón CSIC ORCID; Díaz de Villegas, María D. CSIC ORCID; Gálvez, José A. CSIC ORCID | Palabras clave: | Amino acids Asymmetric synthesis Phosphonates Piperidines Stereoselective reduction |
Fecha de publicación: | 2006 | Editor: | Thieme | Citación: | Synlett (17): 2799-2803 (2006) | Resumen: | Two diastereomeric 4-phosphonomethyl-2-piperidinecarboxylic acids have been prepared in ca. 20% overall yield starting from the easily accessible N-[(S)-1-phenylethyl]-(S)-2,3-di-O-benzylglyceraldimine. The key step for the stereodivergent synthesis is the asymmetric reduction of an exocyclic C=C double bond on a highly functionalized chiral intermediate. This intermediate is obtained by Horner-Wadsworth-Emmons (HWE) reaction of a piperidone derived from the cycloadduct obtained in the aza Diels-Alder reaction between N-[(S)-1-phenylethyl]-(S)-2,3-di-O-benzylglyceraldimine and Danishefsky's diene. In these synthetic routes two new stereogenic centres are created on the piperidine ring with very good or excellent stereoselectivity. | Descripción: | 5 pages. | Versión del editor: | http://dx.doi.org/10.1055/s-2006-950272 | URI: | http://hdl.handle.net/10261/19754 | DOI: | 10.1055/s-2006-950272 | ISSN: | 0936-5214 |
Aparece en las colecciones: | (ICMA) Artículos |
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