title: Dual organocatalytic activation of isatins and formaldehyde tert-butyl hydrazone: asymmetric synthesis of functionalized 3-hydroxy-2-oxindoles.
abstract: Two is better than one! Dual activation of isatins and formaldehyde tert-butyl hydrazone by 2,2'-diamino-1,1'-binaphthalene (BINAM)-derived bis(ureas) is the key to achieve high reactivity and excellent enantioselectivities in the synthesis of azo- and azoxy-functionalized 3-hydroxy-2-oxindoles (see scheme).
authors.affiliation: Departamento de Química Orgánica, Universidad de Sevilla, C/Prof. García González, 1, 41012 Sevilla, Spain.
authors.forename: David
authors.initials: D
authors.lastname: Monge
authors.forename: Ana M
authors.initials: AM
authors.lastname: Crespo-Peña
authors.forename: Eloísa
authors.initials: E
authors.lastname: Martín-Zamora
authors.forename: Eleuterio
authors.initials: E
authors.lastname: Álvarez
authors.forename: Rosario
authors.initials: R
authors.lastname: Fernández
authors.forename: José M
authors.initials: JM
authors.lastname: Lassaletta
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D005557:Formaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry*; D006860:Hydrogen Bonding; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: D006835:Hydrazones; D007211:Indoles; D009281:Naphthalenes; D000078183:Oxindoles; C587307:formaldehyde tert-butyl hydrazone; C022960:2-oxindole; D005557:Formaldehyde; C031721:naphthalene; D007510:Isatin