TADDOL

In organic chemistry, TADDOL is an acronym for α,α,α',α'-tetraaryl-2,2-disubstituted 1,3-dioxolane-4,5-dimethanol. 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.^[2]

References

^ 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<92::AID-ANIE92>3.0.CO;2-K
^ 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

[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<92::AID-ANIE92>3.0.CO;2-K

[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

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