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The present review discusses the versatile applicability and separation mechanisms of thin-layer chromatographic enantiomeric separations. More detailed descriptions will be given for practical applications—separations of underivatized samples—on commercially available, ready-to-use plates, focusing on the thin-layer chromatographic racemate separation based on ligand exchange, which was introduced in 1983 by G�nther et al. (
1
) and on use of a densitometer for determination of antipode distributions at trace level. This chapter will not discuss the numerous and interesting diastereomeric separations by paper and thin-layer chromatography (TLC). We refer to the literature on amino acids (
2
–
8
), peptides, diketopiperazines (
9
–
18
), and other classes of compounds (
19
–
31
).