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(+)-Diethyl L-tartrate is used as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, for Sharpless-type enantioselective oxidation of sulfides to sulfoxides and as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction. It is also used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke therapy.
Peter Somfai. An enantioselective total synthesis of (+)-altholactone from diethyl L-tartrate. Tetrahedron. 1994, 50, (38), 11315-11320.
Woo-Wha Lee.; Sukbok Chang. A new and concise synthetic route to an enantiopure (+)-conduritol-E derivative from diethyl l-tartrate. Tetrahedron: Asymmetry. 1999, 10 (23), 4473-4475.
For use as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, see tert-Butyl hydroperoxide, A13926. For Sharpless-type enantioselective oxidation of sulfides to sulfoxides, see: Org. Synth. Coll., 8, 464 (1993).
For use as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction, see: Chem. Lett., 61 (1992). For a review of the use of tartrate esters as chiral auxiliaries, e.g. in the Simmons-Smith reaction and in 1,3-dipolar cycloaddition reactions, see: Synlett, 1075 (2003).
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