i) (+)-Tartaric acid is one of the by-products of wine making.
- Louis Pasteur’s discovery of enantioisomerism led, in 1874, to the proposal of the
tetrahedral structure of carbon by van’t Hoff and Le Bel.
5.15B CURRENT METHODS FOR RESOLUTION OF ENANTIOMERS
- Resolution via Diastereomer Formation:
- Diastereomers, because they have different melting points, different boiling
points, and different solubilities, can be separated by conventional methods..
- Resolution via Molecular Complexes, Metal Complexes, and Inclusion
Compounds:
- Chromatographic Resolution:
- Kinetic Resolution:
5.16 COMPOUNDS WITH STEREOCENTERS OTHER THAN CARBON
- Stereocenter: any tetrahedral atom with four different groups attached to it.
- Silicon and germanium compounds with four different groups are chiral and the
enantiomers can, in principle, be separated.
R^4 Si R^2
R^1
R^3
Ge R
R 2
1
R^4
R^3
N R
R 2
1
R^4
R^3
+
X−
O S R^2
R^1
2) Sulfoxides where one of the four groups is a nonbonding electron pair are chiral.
3) Amines where one of the four groups is a nonbonding electron pair are achiral
due to nitrogen inversion.