TADDOL

These compounds are easily accessed and are often used as chiral auxiliaries.

[1] TADDOLs consist of a dioxolane ring substituted with two mutually transoid diarylhydroxymethyl Ar2COH) 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.