Ni(II) Schiff-Base Complexes as Chiral Electroauxiliaries and Methodological Platform for Stereoselective Electrochemical Functionalization of Amino Acids.

Abstract

The concept of chiral electroauxiliary based on the redox active chiral platform to perform transformations of a redox inactive substrate is suggested and discussed in the context of the targeted stereoselective electrochemical functionalization of amino acids. Tailor-made amino acids are essential structural features of modern medicinal chemistry and drug design; the development of efficient synthetic approaches to these compounds is of topical interest. The modified substrate (an amino acid) is included as a structural motif in the redox active complex (with a possibility to be released after modification) that integrates "a bifunctional linker" (the structural motif capable to "catch" a substrate) and a chiral moiety responsible for asymmetry induction. The amino acid, being included as a part of such ensemble, becomes stable towards redox destruction and its targeted electrochemical modification saving the amino acid skeleton is possible, thus developing new modes of reactivity for well-known compounds.