Schiff bases are very popular as ligands in coordination chemistry. Plethora of such molecules can be easily obtained by simply varying the nature of the keto and amino precursors. An extremely rich coordination chemistry is generated by the Schiff bases derived from o-vanillin (Hvan). Starting from Hvan and employing chiral amino precursors (amino-КМТНs КnН 1,1′-binaphthyl-β,β′-diamine) chiral ligands are readily obtained. Another useful keto precursor is 3-formyl-salicylic acid (H2fsa). In this communication, we present two families of ligands derived from these keto precursors (Hvan and H2fsa), as well as their complexes. First, we discuss chiral oligonuclear complexes of Co(II), Cu(II), and Mn(III), which are characterized by single crystal X-Ray diffraction, circular dichroism, and magnetic measurements. The binuclear Mn(III) complex is an efficient catalyst for enantioselective reactions.  The self-assembly process between Cu(II) ions and the anionic Schiff base resulting from the condensation reactions between Hvan and R-, respectively, S-methionine generates 1-D coordination polymers. Both enantiomers have been characterized. They exhibit unique two step single-crystal-to-single-crystal transformations, which are accompanied by dramatic changes of their physical properties.