39149-34-3Relevant articles and documents
Mechanochemical Strecker Reaction: Access to α-Aminonitriles and Tetrahydroisoquinolines under Ball-Milling Conditions
Hernández, José G.,Turberg, Mathias,Schiffers, Ingo,Bolm, Carsten
, p. 14513 - 14517 (2016/10/03)
A mechanochemical version of the Strecker reaction for the synthesis of α-aminonitriles was developed. The milling of aldehydes, amines, and potassium cyanide in the presence of SiO2gave the corresponding α-aminonitriles in good to high yields. The high efficiency of the mechanochemical Strecker-type multicomponent reaction allowed the one-pot synthesis of tetrahydroisoquinolines after a subsequent internal N-alkylation reaction.
Efficient asymmetric synthesis of 1-cyano-tetrahydroisoquinolines from lipase dual activity and opposite enantioselectivities in α-aminonitrile resolution
Sakulsombat, Morakot,Vongvilai, Pornrapee,Ramstr?m, Olof
, p. 11322 - 11325 (2014/10/15)
Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic α-aminonitrile compounds are described. α-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, where opposite enantioselectivities could be recorded for certain substrates. Dynamic chemistry: Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic α-aminonitrile compounds are described. α-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, in which opposite enantioselectivities could be recorded for certain substrates (see scheme).
Improved Reagent for Electrophilic Amination of Stabilized Carbanions
Smulik, Jason A.,Vedejs, Edwin
, p. 4187 - 4190 (2007/10/03)
(Equation presented) Enolate amination using O-di(p-methoxyphenyl) phosphinylhydroxylamine 2 is reported. Reagent 2 reacts efficiently with stabilized sodium or potassium enolates derived from malonates, phenylacetates, and phenylacetonitriles and is sufficiently soluble for use in solution at -78°C.