Synthesis of enantioenriched azo compounds: Organocatalytic Michael addition of formaldehyde N-tert-butyl hydrazone to nitroalkenes
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 trans...
| Autores: | , , , , |
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| Formato: | artículo |
| Fecha de publicación: | 2013 |
| País: | España |
| Recursos: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/96617 |
| Acesso em linha: | http://hdl.handle.net/10261/96617 |
| Access Level: | acceso abierto |
| Resumo: | 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. © 2013 The Royal Society of Chemistry. |
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