150024-72-9

Upstream product

• 186581-53-3 diazomethane 
• 50987-15-0 (1S,2S)-(+)-trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 17673-68-6 dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate 
• 106-99-0 buta-1,3-diene 
• 23055-10-9 1,4-dimethyl but-2-enedioate 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 147396-58-5 buta-2,3-dien-1-yl 4-methylbenzenesulfonate 
• 624-49-7 dimethylfumarate 
• 135616-36-3 6,6'-((1E,1'E)-((1S,2S)-cyclohexane-1,2-diylbis(azanylylidene)) bis(methanylylidene))bis(2,4-di-tert-butylphenol) 
• 67-56-1 methanol 
• 31139-02-3 (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid 

Downstream Products

• 140459-96-7 (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester 
• 50987-15-0 (1S,2S)-(+)-trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 167819-32-1 (1R,2R)-α,α,α',α'-tetraphenylcyclohexane-1,2-dimethanol 
• 15679-28-4 ((1R,6R)-6-(hydroxymethyl)cyclohex-3-enyl)methanol 

Relevant academic research and scientific papers

Enantioselective Diels-Alder Reactions of Carboxylic Ester Dienophiles Catalysed by Titanium-Based Chiral Lewis Acid

A new titanium-based chiral Lewis acid 1 has been developed using (1R,2R)-1,2-bis-(2-methoxyphenyl)-ethane-1,2-diol as a chiral vicinal diol ligand. This chiral catalyst was found to exhibit uniformly high enantioselectivity towards carboxylic ester dienophiles in Diels-Alder reactions. The chiral vicinal ligand (1R,2R)-1,2-bis-(2-methoxyphenyl)-ethane-1,2-diol is inexpensive and is easily accessible.

Enantioselective Diels-Alder reactions of optically active (buta-1,3-dien-2-yl)(salen)cobalt(iii) complexes

The syntheses of two optically active (buta-1,3-dien-2-yl)(salen)Co complexes are reported. These dienyl complexes undergo Diels-Alder reactions with high enantioselectivity with a variety of dienophiles. One of the (salen)Co-substituted Diels-Alder cyclo

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.