Diethyl tartrate explained

Diethyl tartrate is an organic compound with the formula (HOCHCO2Et)2 (Et = ethyl). Three stereoisomers exist, R,R-, S,S-, and R,S (=S,R-). They are the ethyl esters of the respective R,R-, S,S-, and R,S-tartaric acids. The R,R- and S,S- isomers are enantiomeric, being mirror images. The meso stereoisomer is not chiral. The chiral isomer is far more common.

In the Sharpless epoxidation, diethyl tartrate and titanium isopropoxide form a chiral catalyst in situ.[1] The TADDOL ligand scaffold is produced from diethyl tartrate.[2]

References

  1. J. Gordon. Hill. K. Barry. Sharpless. Christopher M.. Exon. Ronald. Regenye. 1985. Enantioselective Epoxidation of Allylic Alcohols: (2S,3S)-3-Propyloxiranemethanol. 63. 66. 10.15227/orgsyn.063.0066. Organic Syntheses.
  2. 10.1002/anie.200906550. Enantioselective Gold Catalysis: Opportunities Provided by Monodentate Phosphoramidite Ligands with an Acyclic TADDOL Backbone. Henrik Teller, Susanne Flügge, Richard Goddard, Alois Fürstner. Angew. Chem. Int. Ed.. 49. 2010. 11 . 1949–1953 . 20175172 .

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