TADDOL explained

In organic chemistry, TADDOL is an acronym for . These compounds are easily accessed and are often used as chiral auxiliaries.^[1]

TADDOLs consist of a dioxolane ring substituted with two mutually groups. They are derived from d,l-tartaric acid, an inexpensive C₂-symmetric molecule. Condensation of dimethyl ester of d,l-tartaric acid with acetone gives the acetonide, a particular kind of dioxalane. The ester groups are susceptible to reaction with aryl Grignard reagents, leading after hydrolysis to the diol.^[2]

Notes and References

1. [Dieter Seebach|Seebach, D.]
2. Albert K. Beck, Peter Gysi, Luigi La Vecchia, and Dieter Seebach "(4R,5R)-2,2-Dimethyl-α,α,α',α'-tetra(naphth-2-yl))-1,3-dioxalane-4,5-dimethanol from Dimethyl Tartrate and 2-Naphthyl-Magnesium Bromide" Org. Synth. 1999, 76, 12.