119561-24-9Relevant articles and documents
Biomimetic reductive amination under the continuous-flow reaction conditions
Soloshonok, Vadim A.,Catt, Hector T.,Ono, Taizo
experimental part, p. 261 - 265 (2010/04/05)
This study present a full account of continuous-flow reaction conditions for biomimetic reductive amination of fluorinated carbonyl compounds to corresponding amines and amino acids of biomedical importance. We demonstrate that simple silica-adsorbed DBU can be used as efficient catalysts for on-column 1,3-proton shift reaction, a key transformation in the biomimetic reductive amination process. This new on-column process features operationally convenient conditions, higher chemical yields, enantioselectivity and purity of the corresponding products as compared with traditional in-flask reactions. Moreover the removal of base-catalyst, the most delicate problem of the in-flask reactions, is not an issue in the on-column process, as the silica-adsorbed DBU or polymer-bound guanidine remains on the column and can be reused. This feature renders the overall process substantially more economical and synthetically efficient, in particular, for large-scale synthesis of the corresponding fluorinated amines and amino acids target.
AZOMETHINE-AZOMETHINE ISOMERIZATION IN THE SERIES OF FLUORINE-CONTAINING N-BENZYLIMINES
Soloshonok, V. A.,Gerus, I. I.,Yagupol'skii, Yu. L.,Kukhar', V. G.
, p. 895 - 899 (2007/10/02)
The reaction of N-benzyltriphenylphosphine imide with fluorine-containing carbonyl compounds leads to the corresponding N-benzylimines.The latter readily isomerize under the influence of bases to N-benzylidene derivatives.
