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Synthesis of enantioenriched azo compounds: Organocatalytic Michael addition of formaldehyde N-tert-butyl hydrazone to nitroalkenes

 

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Opened Access Synthesis of enantioenriched azo compounds: Organocatalytic Michael addition of formaldehyde N-tert-butyl hydrazone to nitroalkenes
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Author: Monge Fernández, David
Daza Sánchez, Silvia
Bernal Fernández, Pablo
Fernández Fernández, Rosario Fátima
Lassaletta Simón, José María
Department: Universidad de Sevilla. Departamento de Química orgánica
Date: 2013
Published in: Organic and Biomolecular Chemistry, 11, 326-335.
Document type: Article
Abstract: The unprecedented diaza-ene reaction of formaldehyde N-tert-butyl hydrazone with nitroalkenes can be efficiently catalyzed by an axially chiral bis-thiourea to afford the corresponding diazenes in good to excellent yields (60-96%) and moderate enantioselectivities, up to 84 : 16 er; additional transformation of diazenes into their tautomeric hydrazones proved to be operationally simple and high-yielding, affording bifunctional compounds which represent useful intermediates for the synthesis of enantioenriched β-nitro-nitriles and derivatives thereof.
Cite: Monge Fernández, D., Daza Sánchez, S., Bernal Fernández, P., Fernández Fernández, R.F. y Lassaletta Simón, J.M. (2013). Synthesis of enantioenriched azo compounds: Organocatalytic Michael addition of formaldehyde N-tert-butyl hydrazone to nitroalkenes. Organic and Biomolecular Chemistry, 11, 326-335.
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URI: https://hdl.handle.net/11441/70648

DOI: 10.1039/c2ob26963e

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