Article
Synthesis of enantioenriched azo compounds: Organocatalytic Michael addition of formaldehyde N-tert-butyl hydrazone to nitroalkenes
Author/s | 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 |
Publication Date | 2013 |
Deposit Date | 2018-02-27 |
Published in |
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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 ... 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. |
Funding agencies | Ministerio de Ciencia e Innovación (MICIN). España Junta de Andalucía |
Project ID. | CTQ2010-15297
CTQ2010-14974 2008/ FQM-3833 2009/FQM-4537 |
Citation | 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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