75158-10-0Relevant articles and documents
Asymmetric strecker reaction with chiral amines: A catalyst-free protocol using acetone cyanohydrin in water
Pori, Matteo,Galletti, Paola,Soldati, Roberto,Giacomini, Daria
, p. 1683 - 1695 (2013/04/10)
The synthesis of a series of new chiral α-aminonitriles was achieved in a diastereoselective Strecker reaction in a one-pot procedure with aldehydes, enantiopure amines, and acetone cyanohydrin in water. Primary and secondary amines derived from L-α-amino acids were used as sources of chirality. The reactions proceeded efficiently without any catalyst at room temperature. The diastereoselectivity of the process, and the configurational stability of new chiral α-aminonitriles were investigated. The identification of labile intermediates by NMR analysis, and a proposed mechanism and a model for the asymmetric induction are reported. The chemical transformation of proline-derived chiral α-amino-nitriles into chiral amino-diacids, aminols, and amides is reported. A series of new chiral α-aminonitriles was obtained in a diastereoselective Strecker reaction. Aldehydes were coupled with enantiopure amines derived from L-proline, L-phenylglycine, L-phenyl alanine, and L-tryptophan, in a one-pot procedure using acetone cyanohydrin in water. Copyright
Iodine as a novel and efficient reagent for the synthesis of α-aminonitriles by a three-component condensation of carbonyl compounds, amines, and trimethylsilyl cyanide
Royer, Laurel,De, Surya K.,Gibbs, Richard A.
, p. 4595 - 4597 (2007/10/03)
A straightforward and general method has been developed for the synthesis of α-aminonitriles by simply combining aldehydes or ketones, amines, and trimethylsilyl cyanides in the presence of a catalytic amount of molecular iodine at room temperature.
Lithium perchlorate/diethylether catalyzed aminocyanation of aldehydes
Heydari, Akbar,Fatemi, Parinaz,Alizadeh, Abdol-Ali
, p. 3049 - 3050 (2007/10/03)
A simple and efficient one-pot method was developed to give α- aminonitriles from aldehydes + amines + TMSCN in LPDE. Optically active α- aminonitriles were snythesized by using (S)-(-)- or (R) (+) α- methylbenzylamine, (S)-(-) α-methylbenzylamine affords