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

AuthorsMonge, David; Daza, S.; Bernal, Pablo; Fernández, Rosario; Lassaletta, José M.
Issue Date2013
PublisherRoyal Society of Chemistry (UK)
CitationOrganic and Biomolecular Chemistry 11: 326- 335 (2013)
AbstractThe 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.
Identifiersdoi: 10.1039/c2ob26963e
issn: 1477-0520
Appears in Collections:(IIQ) Artículos
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