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Effect of substituents on the configurational stability of the stereogenic nitrogen in metal(II) complexes of α‐amino acid Schiff bases
Author(s) -
Mei Haibo,
Jean Marion,
Albalat Muriel,
Vanthuyne Nicolas,
Roussel Christian,
Moriwaki Hiroki,
Yin Zizhen,
Han Jianlin,
Soloshonok Vadim A.
Publication year - 2019
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23066
Subject(s) - stereocenter , chemistry , steric effects , metal , nitrogen , amino acid , stereochemistry , computational chemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry
Herein, we report a general method for quantitative measurement of the configurational stability of the stereogenic nitrogen coordinated to M (II) in the corresponding square planar complexes. This stereochemical approach is quite sensitive to steric and electronic effects of the substituents and shown to work well for Ni(II), Pd(II), and Cu(II) complexes. Structural simplicity of the compounds used, coupled with high sensitivity and reliability of experimental procedures, bodes well for application of this approach in evaluation of chemical stability and stereochemical properties of newly designed chiral ligands for general asymmetric synthesis of tailor‐made amino acids.