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Título: | Highly diastereoselective cyanation of methyl ketimines obtained from (R)-glyceraldehyde |
Autor: | Badorrey, Ramón CSIC ORCID; Cativiela, Carlos CSIC ORCID; Díaz de Villegas, María D. CSIC ORCID; Díez, Roberto; Galbiati, Fabrizio; Gálvez, José A. CSIC ORCID | Fecha de publicación: | 2005 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 70(24): 10102-10105 (2005) | Resumen: | Addition of trimethylsilyl cyanide to ketimines derived from (R)-2,2-dimethyl-1,3-dioxolan-4-yl methyl ketone to generate a quaternary stereocenter has been achieved with high yields and excellent diastereoselectivity. The stereoselectivity was found to be temperature and solvent dependent. The β-hydroxy-α-amino nitrile of syn configuration was the major compound in kinetically controlled reactions, whereas the anti stereoisomer was obtained in excess in thermodynamically controlled reactions. Double stereodifferentiation under kinetic control conditions was successful, and the cyanation reaction occurred with complete syn diastereoselectivity using the matched pair. The versatility of the resulting amino nitrile as a synthetic intermediate was tested by performing the synthesis of orthogonally protected (R)-(2-aminomethyl)alanine. | Versión del editor: | https://doi.org/10.1021/jo051592c | URI: | http://hdl.handle.net/10261/271762 | DOI: | 10.1021/jo051592c | ISSN: | 0022-3263 |
Aparece en las colecciones: | (ICMA) Artículos |
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