Racemization versus retention of chiral information during the formation of silicon and tin complexes with chiral Schiff base ligands

► The reactivity of chiral Schiff base ligands with O,N,O′-coordination ability was explored. ► Reaction with SiCl4 in presence of triethylamine leads to planarization of the ligands. ► Reaction with SiCl4 without triethylamine leads to racemization of the amino acid ester. ► A unifying mechanism for the formation of both products has been proposed. ► It is possible to retain the chiral information in reactions with R2SnCl2.