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Título: | First asymmetric synthesis of an acyclic β,β-dialkylated-γ-aminobutyric acid |
Autor: | Aguirre, Daniel; Cativiela, Carlos CSIC ORCID; Díaz de Villegas, María D. CSIC ORCID; Gálvez, José A. CSIC ORCID | Palabras clave: | γ-Amino acids Asymmetric synthesis Diastereoselective alkylation |
Fecha de publicación: | 21-ago-2006 | Editor: | Elsevier | Citación: | Tetrahedron 62(34): 8142-8146 (2006) | Resumen: | Enantiomerically pure (R)-γ-amino-β-benzyl-β-methylbutyric acid, an acyclic β,β-dialkyl GABA derivative, is efficiently synthesised from (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate by a sequence based on benzylation, Arndt–Eistert homologation and nitrile reduction. Benzylation of (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using potassium carbonate under not strictly anhydrous conditions occurs diastereoselectively to afford (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (S)-2-cyano-2-methyl-3-phenylpropanoate, the key chiral intermediate from which the desired γ-amino acid is obtained in five steps in 65% overall yield. | Descripción: | 5 pages, 2 schemes, 1 figure. | Versión del editor: | http://dx.doi.org/10.1016/j.tet.2006.06.021 | URI: | http://hdl.handle.net/10261/19047 | DOI: | 10.1016/j.tet.2006.06.021 | ISSN: | 0040-4020 |
Aparece en las colecciones: | (ICMA) Artículos |
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