1056017-09-4Relevant academic research and scientific papers
Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones
Martinez-Munoz, Aurora,Monge, David,Martin-Zamora, Eloisa,Marques-Lopez, Eugenia,Alvarez, Eleuterio,Fernandez, Rosario,Lassaletta, Jose M.
, p. 8247 - 8255 (2013)
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.
Uncatalyzed Strecker-type reaction of N,N-dialkylhydrazones in pure water
Marques-Lopez, Eugenia,Herrera, Raquel P.,Fernandez, Rosario,Lassaletta, Jose M.
experimental part, p. 3457 - 3460 (2009/04/08)
Aldehyde and ketone N,N-dialkylhydrazones behave as a stable class of imine surrogates exhibiting a unique reactivity in the Strecker reaction with in situ generated HCN, that proceeds in pure water in the absence of co-solvents, catalysts or promoters. E
