title: Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones.
abstract: The enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones is presented. Using trimethylsilyl cyanide (TMSCN) as the cyanide source, the reaction can be efficiently catalyzed by a tert-leucine-derived bifunctional thiourea to afford the corresponding hydrazino nitriles in good to excellent yields (50-96%) and moderate to good enantioselectivities, up to 86% ee. Further transformations of the nitrile functionality allow access to useful protected hydrazino acids and imidazolidinones. Interestingly, some of the hydrazino nitriles and their derivatives could be recrystallized in high recovery, yielding essentially pure enantiomers.
authors.affiliation: Departamento de Química Orgánica, Universidad de Sevilla, C/ Prof. García González, 1, 41012 Sevilla, Spain. dmonge@us.es ffernan@us.es.
authors.forename: Aurora
authors.initials: A
authors.lastname: Martínez-Muñoz
authors.forename: David
authors.initials: D
authors.lastname: Monge
authors.forename: Eloísa
authors.initials: E
authors.lastname: Martín-Zamora
authors.forename: Eugenia
authors.initials: E
authors.lastname: Marqués-López
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; D006835:Hydrazones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D006835:Hydrazones; D009570:Nitriles; D013890:Thiourea