367944-99-8Relevant academic research and scientific papers
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)
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
