146499-09-4

Upstream product

• 119-61-9 benzophenone 
• 608-68-4 dimethyl L-tartrate 
• 2235-01-0 dimethoxydiphenylmethane 

Downstream Products

• 1209050-64-5 (R,R)-2,2-diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid 
• 126524-74-1 (4R,5R)-2,2-diphenyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanol 

Relevant academic research and scientific papers

Cyclic ketals of tartaric acid: Simple and tunable reagents for the determination of the absolute configuration of primary amines

(Figure Presented) 2,2Diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid (DPD) and 2,2-dinaphthalen-2-yl-[1,3]dioxolane-4,5-dicarboxylic acid (DND) have been synthesized starting from dimethyl tartrate. DPD and DND amides of α-chiral primary amines showed significantly different 1H chemical shift values depending on the stereochemistry of the derivatizing agent. On the basis of this chemical shift difference, the absolute configuration of amine substrates could be assigned. DND amides showed significantly larger chemical shift differences than the corresponding DPD amides allowing for a more error-free assignment.

Enantioselective photocycloaddition mediated by chiral Bronsted acids: Asymmetric synthesis of the rocaglamides

Enantioselective syntheses of methyl rocaglate and the related natural products rocaglamide and rocaglaol are outlined. The approach involves enantioselective [3 + 2] photocycloaddition promoted by chiral Bronsted acids (TADDOLs) to afford an aglain precursor followed by a ketol shift/reduction sequence to the rocaglate core. Copyright

On the origin of changes in topicity observed in Diels-Alder reactions catalyzed by Ti-TADDOLates

New C2 symmetric TADDOLs containing different groups at the 2-position of the dioxolane ring have been prepared. The Ti catalysts derived from these have been studied in the Diels-Alder reaction of cyclopentadiene and (E)-2-butenoyl-1,3-oxazolidin-2-one. Substituents at the C-2 position of the dioxolane ring can play an important role in determining the selectivity as well as the nature of the major isomer. This effect is more important for TADDOLs containing bulky aromatic groups such as 3,5-dimethylphenyl- or 1-naphthyl at the α-positions. Experimental evidence supports the hypothesis that π-π interactions between aromatic groups at the C-2 and the ones at the α-positions are critical in this respect.

Reduction of Ketones with LiAlH4 Complexes of α,α,α′,α′-Tetraaryl-1,3-dioxolane-4,5- dimethanols (TADDOLs): A Combination of Enantioselective Reduction and Clathrate Formation with a Discussion of LAH Reagents Bearing C2-Symmetrical Ligands

A complex prepared from one equivalent each of LiAlH4, EtOH and a TADDOL (α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5- dimethanol) reduces aryl alkyl ketones to sec. alcohols with enantiomer ratios (er) up to 96:4. The chiral LAH derivative is used in two-fold excess in THF solution and at dry ice temperatures. The ability of TADDOLs to form clathrates diastereoselectively can be exploited to increase the er of the initially formed alcohols by a simple modification of the work-up procedure and hence, products of very high enantiopurity (er 99:1) can be isolated. When (R,R)-TADDOLs (from (R,R)-tartrate) are applied in the reaction, the 1-aryl-alkanols formed preferentially have (S) configuration, as for the products obtained with the corresponding (P)-BINOL and (P)-BIPHENOL derivatives. A common mechanistic model is discussed.

SYNTHESIS AND STRUCTURE OF (4R,5R)-α,α,α',α'-2,2-HEXAPHENYL-4,5-DIMETHANOL-1,3-DIOXOLANE

We report the synthesis of the 1,4-diol 2 (4R,5R)-α,α,α',α-2,2-hexaphenyl-4,5-dimethanol-1,3-dioxolane from dimethyl-L-tartrate and benzophenone.The X-ray and the IR structural studies on 2 show that this compound has a preferred conformation with OH --- Ph interactions which are different from related compounds.