100722-18-7Relevant academic research and scientific papers
One-Pot Synthesis of α-Amino Nitrile Units through Alkylative Strecker Cyanation from Formamides
Yu, Bao,Bodinier, Florent,Saague-Tenefo, Maximiliene,Gerardo, Patrice,Ardisson, Janick,Lannou, Marie-Isabelle,Sorin, Geoffroy
, p. 3634 - 3640 (2021/07/22)
In this work, we describe the one-pot synthesis of α-amino nitrile units by the concomitant addition of alkyl (or aryl) Grignard reagents and TMS cyanide through alkylative Strecker cyanation from readily available formamides. The reaction is broad in sco
Preparation of non-racemic single-stereocentre α-aminonitriles and a study of their fate in Bruylants reactions
Beaufort-Droal, Virginie,Pereira, Elisabeth,Théry, Vincent,Aitken, David J.
, p. 11948 - 11954 (2007/10/03)
A number of chiral carboxamide dehydration methods were investigated for the preparation of four representative enantiomerically enriched α-aminonitriles possessing only one stereogenic centre; best results were observed using Burgess' salt (yield up to 87%, er up to 92/8) or the trifluoroacetic anhydride-triethylamine combination (yield up to 98%, er up to 86/14). Two of the aminonitriles thus obtained were subjected to Bruylants reactions with a methyl Grignard reagent to furnish the corresponding tertiary amines; these products, along with any unreacted starting materials, were obtained essentially in racemic form. In accord with the accepted mechanism for this reaction, a magnesium species is implicated in the formation of an iminium, the common intermediate for both chemical transformation and racemization processes.
