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Dimethyl L-tartrate is a chiral auxiliary used for the enantioselective epoxidation of allylic alcohols. It is used for asymmetric α-halogenation of acetals. It is a starting material for the synthesis of chiral building blocks.
Nobuo Nagashima; Masaji Ohno. An efficient O-monoalkylation of dimethyl L-tartrate via O-stannylene acetal with alkyl halides in the presence of cesium fluoride. Chemistry Letters. 1987, 16,(1), 141-144.
Thierry Buffeteau; Laurent Ducasse; Aurelie Brizard; Ivan Huc; Reiko Oda. Density functional theory calculations of vibrational absorption and circular dichroism spectra of dimethyl-L-tartrate. J. Phys. Chem. A. 2004, 108,(18), 4080-4086.
Has been used in Sharpless epoxidation of allylic alcohols; see tert-Butyl hydroperoxide, A13926.
Cyclic ketals formed with dimethyl tartrate as the diol component undergo highly selective bromination: Angew. Chem. Int. Ed., 25, 259 (1986).