Artículo
Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones
Autor/es | Martínez Muñoz, Aurora
Monge Fernández, David Martín Zamora, Eloísa Marqués López, Eugenia Álvarez González, Eleuterio Fernández Fernández, Rosario Fátima Lassaletta, José M. |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2013 |
Fecha de depósito | 2018-02-21 |
Publicado en |
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Resumen | The enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones is presented. Using trimethylsilyl cyanide (TMSCN) as the cyanide source, the reaction can be efficiently catalyzed by a ... The enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones is presented. Using trimethylsilyl cyanide (TMSCN) as the cyanide source, the reaction can be efficiently catalyzed by a tert-leucine-derived bifunctional thiourea to afford the corresponding hydrazino nitriles in good to excellent yields (50-96%) and moderate to good enantioselectivities, up to 86% ee. Further transformations of the nitrile functionality allow access to useful protected hydrazino acids and imidazolidinones. Interestingly, some of the hydrazino nitriles and their derivatives could be recrystallized in high recovery, yielding essentially pure enantiomers. |
Agencias financiadoras | Ministerio de Ciencia e Innovación (MICIN). España Junta de Andalucía |
Identificador del proyecto | CTQ2010-15297
CTQ2010-14974 2008/FQM-3833 2009/FQM-4537 |
Cita | Martínez Muñoz, A., Monge Fernández, D., Martín Zamora, E., Marqués López, E., Álvarez González, E., Fernández Fernández, R.F. y Lassaletta Fernández, J.M. (2013). Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones. Organic and Biomolecular Chemistry, 11, 8247-8255. |
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