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Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones

AuthorsMartínez-Muñoz, A.; Monge, David; Martín-Zamora, Eloísa; Marqués-López, Eugenia ; Álvarez, Eleuterio ; Fernández, Rosario; Lassaletta, José M.
Issue Date2013
PublisherRoyal Society of Chemistry (UK)
CitationOrganic and Biomolecular Chemistry 11: 8247- 8255 (2013)
AbstractThe 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. © 2013 The Royal Society of Chemistry.
Identifiersdoi: 10.1039/c3ob41437j
issn: 1477-0520
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