Description
(-)-Dipivaloyl-l-tartaric acid is mainly used as a chiral resolving agent to resolve racemic compounds such as amines, and can also be used as a ligand/intermediate in organic synthesis.
Chemical Properties
white to light yellow crystal powde
Uses
(?)-O,O′-Di-pivaloyl-L-tartaric acid can be used:
- As a chiral staple in the synthesis of helical π-conjugated cyclic nanocoils, which are used as nano springs, nano solenoids, and pressure sensors.
- As an additive in the iridium-catalyzed C-H amidation reactions of arylphosphoryl compounds.
Application
(2R,3R)-Dipivaloyltartaric Acid is used as a chiral auxiliary for enantioselective protonation (deracemization) and asymmetric transformation; starting
material for synthesis of chiral succinimides and polyhydroxy compounds.
Preparation
Preparative Method of (2R,3R)-Dipivaloyltartaric Acid: hydrolysis of the corresponding anhydride obtained by heating (2R,3R)-tartaric acid and
pivaloyl chloride at 120-140 °C for 4 h.[1] Drying: over P2O5 in vacuo, controlled by 1H NMR and optical
rotations.
storage
(2R,3R)-Dipivaloyltartaric Acid anhydrous solid can be stored at rt in the absence of moisture. It is
retrievable from its basic solution (10 % aq NaHCO3), after acidification (HCl), with a quantitative yield.2 On
heating it transforms into an anhydride with elimination of one molecule of water.
References
1. Duhamel, L.; Plaquevent, J. C. OPP 1982, 14, 347.
