TADDOL

Structure of a generic TADDOL (Ar = aryl, Me = methyl.

In organic chemistry, TADDOL is an acronym for α,α,α',α'-tetraaryl-2,2-disubstituted 1,3-dioxolane-4,5-dimethanol. Despite their complicated full name, these compounds are easily accessed and are often used in 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.^[2]

References

1. Seebach, D.; Beck, A. K.; Heckel, A., "TADDOLs, their derivatives, and TADDOL analogs: versatile chiral auxiliaries", Angew. Chem. Int. Ed. 2001, 40, 92-138. doi:10.1002/1521-3773(20010105)40:1
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. doi: 10.15227/orgsyn.076.0012