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TADDOL
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.〔Seebach, D.; Beck, A. K.; Heckel, A., "TADDOLs, their derivatives, and TADDOL analogs: versatile chiral auxiliaries", Angew. Chem., Int. Ed. 2001, 40, 92-138. 〕 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.〔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. 〕 ==References== 〔
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