167282-09-9

Upstream product

• 88797-37-9 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxyl dichloride 
• 177283-77-1 (4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 63126-29-4 (4R,5R)-2,2,N,N,N',N'-hexamethyl-1,3-dioxolane-4,5-dicarboxamide 
• 100-59-4 phenylmagnesium chloride 

Downstream Products

• 861853-87-4 (1R,2R,3R,4R)-1,4-Dimethoxy-1,4-diphenyl-butane-2,3-diol 
• 3966-32-3 (R)-methoxyphenylacetic acid 
• 17628-72-7 R-(-)-2-methoxy-2-phenyl ethanol 
• 72538-27-3 (-)-(R)-2-methoxy-2-phenylacetaldehyde 
• 647027-99-4 (4S,5S)-4,5-bis[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane 
• 929217-58-3 (-)-[(4R,5R)-2,2-dimethyl-5-((R)-2,2,2-trifluoro-1-hydroxy-1-phenylethyl)-[1,3]dioxolan-4-yl]phenylmethanone 
• 167640-30-4 (αR,α'R,4R,5R)-2,2,α,α'-tetramethyl-α,α'-diphenyl-1,3-dioxolane-4,5-dimethanol 
• 167640-32-6 (αS,α'S,4R,5R)-2,2,α,α'-tetramethyl-α,α'-diphenyl-1,3-dioxolane-4,5-dimethanol 
• 929217-56-1 (-)-[(4R,5R)-2,2-dimethyl-5-((R)-2,2,2-trifluoro-1-phenyl-1-(trimethylsilanyloxy)ethyl)-[1,3]dioxolan-4-yl]phenylmethanone 

Relevant academic research and scientific papers

Synthesis of enantiopure trifluoromethyl building blocks via a highly chemo- and diastereoselective nucleophilic trifluoromethylation of tartaric acid-derived diketones

(Chemical Equation Presented) A highly diastereoselective nucleophilic mono(trifluoromethylation) of a tartaric acid-based diketone, using trifluoromethyl(trimethyl)silane, afforded the corresponding γ-keto trifluoromethylcarbinol. The scope and limitation of this reaction was studied. The acidic removal of the acetonide moiety protecting the two hydroxyl groups of the adducts was unsuccessful. Bis(O-methylation) of the aromatic derivatives under basic conditions, followed by acidic hydrolysis and oxidative cleavage, led to two different enantiopure products: an α-aryl-α-methoxy- α-trifluoromethyl ethanal and an α-aryl-α-methoxycarboxylic acid. The overall process is eventually an interesting way to convert one natural chiral raw material into two functionalized enantiopure building blocks including a trifluoromethyl one.

A new access to enantiopure syn- and anti-2-methyl-1,3-diol moieties from chiral nonracemic α-bromo α′-sulfinyl ketones promoted by samarium diiodide

syn- and anti-2-Methyl-1,3-diols have been prepared by a two-step sequence that involves a SmI2-promoted stereoselective Reformatsky addition of chiral nonracemic α-bromo α′-sulfinyl ketones to various aldehydes followed by stereoselective redu

Nucleophilic addition reactions of 1,4-diketones derived from tartaric acid: Synthesis of TADDOL analogues

A systematic investigation of the reduction and Grignard reagents addition to 1,4-diketones derived from tartaric acid was carried out. It was found that the reduction proceeded with high selectivity using K-Selectride as the reducing agent; while Grignar

Asymmetric synthesis of both enantiomers of α-methyl-α-methoxyphenylacetic acid from l-(+)-tartaric acid: formal enantioselective synthesis of insect pheromone (-)-frontalin

Both antipodes of α-methyl-α-methoxyarylacetic acid derivatives were prepared from a common chiralpool precursor l-(+)-tartaric acid. The key step involves the addition of Grignard reagents to 1,4-diketones derived from tartaric acid. The utility of this

Asymmetric synthesis of α-methoxyarylacetic acid derivatives

Stereoselective synthesis of a series of 2-aryl-2-methoxyethanols was achieved from inexpensive chiral pool tartaric acid employing a diastereoselective reduction of a symmetrical 1,4-diaryldiketone as the key step. 2-Aryl-2-methoxyethanols were enantioselectively prepared in 80-90% yield

Synthesis of C2-symmetric 1,4-diketones from tartaric acid dichloride

Cross-coupling reactions of tartaric acid dichloride with organocopper reagents, derived from Grignard reagents, cuprous bromide and lithium bromide, provide a simple and straightforward method for the synthesis of C2-symmetric 1,4-diketones.

Selective addition of Grignard reagents to 2,3-O-isopropylidene bis-Weinreb tartaric acid amide

Controlled addition of Grignard reagents to tartaric acid derived bis-Weinreb amide 3 provides a facile, direct entry to desymmetrized 1,4-functionalized-syn-2,3-diol intermediates 4 and to C2-symmetrical 1,4-diketones 5. The synthetic versatil

Preparation and Structural Analysis of Several New α,α,α',α'-Tetraaryl-1,3-dioxolane-4,5-dimethanols (TADDOL's) and TADDOL Analogs, Their Evaluation as Titanium Ligands in the Enantioselective Addition of Methyltitanium and Diethylzinc Reagents to Benzaldehyde, and Refinement of ...

Preparation and screening of twenty new ligands, all analogs of α,α,α',α'-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL), for the Ti-catalyzed asymmetric addition of methyltri(isopropoxy)titanium and diethylzinc to benzaldehyde are described.These ligands have the dioxolane ring of the TADDOL's replaced by cyclobutane, cyclopentane, cyclohexene, cyclohexane, bicycloheptene and -heptane and bicyclooctene and -octane moieties; several have H-atoms or alkyl groups in place of the aryl groups, and nine of them have C2 symmetry.X-Ray crystallography and molecular mechanics are used to analyze the structure of the ligands, and two structural features appear to correlate with selectivity: i) the torsion angle for the chelating O-atom and the ortho-C-atom of the axial Ph group (a small, ca. 19 deg, angle is optimum, Fig. 8) and ii) the "degree of perpendicularity" of the axial Ph group (Fig. 9).Competition experiments indicate that TADDOL 1a catalyzes both the methyltitanium and diethylzinc additions >/= 50 times faster than the related dioxolane analogs 12a, 12c, and 12e (Scheme 7), indicating that both axial and equatorial aryl groups (see Footnote 6) are necessary for ligand-accelerated catalysis of these reactions.A refined mechanistic hypotesis is presented (Fig. 10) to explain the selectivities observed for these new ligands.Our analysis suggests that a combination of structural features appear necessary for good catalytic efficiency and high selectivity.These features, especially the rather subtle conformational effects, appear to be optimized (among the ligands tested) in the TADDOL's.