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Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones

 

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Opened Access Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones
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Author: Martínez Muñoz, Aurora
Monge Fernández, David
Martín Zamora, Eloísa
Marqués López, Eugenia
Álvarez González, Eleuterio
Fernández Fernández, Rosario Fátima
Lassaletta, José M.
Department: Universidad de Sevilla. Departamento de Química orgánica
Date: 2013
Published in: Organic and Biomolecular Chemistry, 11, 8247-8255.
Document type: Article
Abstract: 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.
Cite: 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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URI: https://hdl.handle.net/11441/70493

DOI: 10.1039/c3ob41437j

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