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The Elaboration of a General Approach to the Asymmetric Synthesis of 1,4‐Substituted 1,2,3‐Triazole Containing Amino Acids via Ni(II) Complexes
Author(s) -
Larionov Vladimir A.,
Adonts Hovhannes V.,
Gugkaeva Zalina T.,
Smol'yakov Alexander F.,
Saghyan Ashot S.,
Miftakhov Mansur S.,
Kuznetsova Svetlana A.,
Maleev Victor I.,
Belokon Yuri N.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800228
Subject(s) - chemistry , benzophenone , amino acid , click chemistry , combinatorial chemistry , aqueous solution , ligand (biochemistry) , alkyne , side chain , triazole , 1,2,4 triazole , iodide , stereochemistry , catalysis , medicinal chemistry , organic chemistry , biochemistry , polymer , receptor
Herein we report a general method of the asymmetric synthesis of 1,4‐substituted 1,2,3‐triazole containing amino acids via copper(I) iodide catalyzed “click reaction” between azides and chiral Ni(II) complexes of Schiff bases of ( S )‐ or ( R )‐BPB with alkyne side chain derivatised amino acids. The final Ni(II) complexes were decomposed with aqueous HCl and the 1,4‐substituted 1,2,3‐triazole containing amino acids isolated with excellent enantioselectivities (>99% ee ). The chiral auxiliary ligand (BPB= N ‐benzyl proline benzophenone) can be recycled and reused for the synthesis of starting Ni(II) complexes.