Synthesis and properties of α-aminonitriles

Enantioselective Strecker Reactions between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides

“…[11f][11g] We therefore assumed that the transition states of the chiral N-oxide-promoted Strecker reactions should be hypervalent silicates. [23] In order to confirm the hypothesis, 29 Si NMR (300 MHz) analyses were carried out at 25°C in CDCl 3 . Firstly, all experiments were performed in CDCl 3 , as detailed in the Exp.…”

“…[1] Together with the classic Strecker reaction, [2] one of the most important reactions for the production of α-amino nitriles Ϫ key intermediates for the synthesis of α-amino acids Ϫ is asymmetric cyanation of imines (Scheme 1). [3] Several procedures requiring the use of chiral auxiliaries have been reported to afford α-amino nitriles with high selectivity. [4] However, the enantioselective addition of cyanide to imine through the employment of chiral ligands [5,6] and chiral promoters can be regarded as one of the most attractive strategies.…”

2-Amino-2-alkyl(aryl)propanenitriles as key building blocks for the synthesis of five-membered heterocycles

“…3 Bifunctional 2-amino-2-alkyl(aryl)propanenitriles contain in their molecules both a nucleophilic centre at amino group and an electrophilic centre at cyano group, which is advantageous from the standpoint of their applications as basic synthetic building blocks used for syntheses of a large number of organic compounds. [4][5][6][7] The aim of this review article is to summarize trends -particularly those appearing during the last decade -in the application possibilities of 2-amino-2-alkyl(aryl)propanenitriles as the key precursors for syntheses of five-membered heterocycles. The paper discusses the conditions of these syntheses, the physico-chemical properties or also the application possibilities of the heterocyclic compounds prepared from 2-amino-2-alkyl(aryl)propanenitriles (Scheme 1).…”

Enantioselective Strecker Reactions Between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides.

“…[3] Several procedures requiring the use of chiral auxiliaries have been reported to afford α-amino nitriles with high selectivity. [4] However, the enantioselective addition of cyanide to imine through the employment of chiral ligands [5,6] and chiral promoters can be regarded as one of the most attractive strategies.…”