61878-73-7

Upstream product

• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 6084-15-7 2-iodo-1-phenylpropan-1-one 
• 100-52-7 benzaldehyde 
• 124659-36-5 2-(3-Methyl-2-phenyl-2,3-dihydro-benzothiazol-2-yl)-1-phenyl-propan-1-one 
• 137604-19-4 Lithium; 1-phenyl-prop-2-en-1-olate 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 
• 1846-29-3 1,3-diphenyl-2-methylpropane-1,3-dione 
• 57204-88-3 propiophenone lithium enolate 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 19347-08-1 acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester 
• 768-03-6 Phenyl vinyl ketone 
• 4393-06-0 1-Phenyl-2-propen-1-ol 

Downstream Products

• 1846-29-3 1,3-diphenyl-2-methylpropane-1,3-dione 
• 366487-68-5 (1S,3S)-2-methyl-1,3-diphenylpropane-1,3-diol 

Relevant academic research and scientific papers

Highly stereoselective metal-mediated domino aldol reactions of propiophenone enolates with heteroaromatic, aliphatic, and unsaturated aldehydes

The one-pot reaction of propiophenone with heteroaromatic, aliphatic, and unsaturated aldehydes in the presence of metal halides furnishes racemic tetrahydro-2H-pyran-2,4-diols in a highly diastereo-selective manner. The mechanism for the stereoselective

The Polymer Effect on Catalysts. Aldimine-Selective Reactions in the Coexistence of Aldehydes Using a Polymer-Supported Scandium Catalyst

Aldimine-selective reactions in the coexistence of aldehydes using a polymer-supported scandium catalyst have been developed. These are remarkable examples of the polymer effect on catalysts to increase selectivities, which can be explained by the stabili

Iron-Modified Mesoporous Silica as an Efficient Solid Lewis Acid Catalyst for the Mukaiyama Aldol Reaction

Fe-MCM-41 and Fe-SBA-15, two different iron-containing mesoporous silicas, were successfully synthesized by a straightforward and versatile method using iron acetylacetonate as a metal precursor. pH adjustment with ammonia during the synthesis was found t

Synthesis of a Bolm's 2,2′-Bipyridine Ligand Analogue and Its Applications

A new method of synthesis of an analogue of Bolm's 2,2′-bipyridine ligand based on the catalytic [2+2+2] cyclotrimerization of 1-halodiynes with nitriles was developed. Crucial step of the whole synthesis turned out to be homodimerization of a substituted 2-bromopyridine to the corresponding bipyridine, that was studied and optimized. The newly prepared bipyridine (S,S)-2 was then tested as a chiral ligand in metal-catalyzed enantioselective reactions. Out of the studied reactions the most promising results were obtained in epoxide ring opening (82% yield, 98% ee) and Mukaiyama aldol reaction (>96% yield, 99/1 dr, 92% ee). In the case of Mukaiyama-aldol reaction as well as in the Michael addition, novel ligand 2 proved its robustness compared to Bolm's ligand as it was less sensitive to the purity of used reagents. (Figure presented.).

Self-Assembled Single-Walled Metal-Helical Nanotube (M-HN): Creation of Efficient Supramolecular Catalysts for Asymmetric Reaction

Ever since the axial chiral catalysts were developed for asymmetric reactions with excellent chiral discrimination and high efficiencies, the interest in the supramolecular catalyst has also been extensively investigated. Here, with a hint from the typical molecular catalyst, we developed a series of metal-coordinated nanotube (M-helical nanotube, M-HN) catalysts for asymmetric reactions. The M-HN catalyst was fabricated on the basis of the self-assembly of an l-glutamic acid terminated bolaamphiphile, which formed a single-walled nanotube. On one hand, through the coordination of transition metal ions with the carboxylic acid groups on the nanotube surface, a wide variety of single-walled M-HN catalysts could be fabricated, in which the coordination sites could serve as the catalytic sites. On the other hand, using a slight amount of these catalysts, significant reactivity and enantioselectivity were realized for certain asymmetric reactions under mild conditions. Remarkably, Bi(III)-HN could catalyze the asymmetric Mukaiyama aldol reaction with high enantioselectivity (up to 97% ee) in an aqueous system; Cu(II)-HN catalyzed the asymmetric Diels-Alder reaction with up to 91% ee within 60 min. It was suggested that a synergetic effect of the aligned multicatalytic sites and stereochemical selectivity of the M-HN lead to an excellent catalytic performance. Through this work, we proposed a new concept of a single-walled nanotube as catalyst and showed the first example of nanotube catalysts presenting high reactivity and enantioselectivity that rivaled a chiral molecular catalyst.

Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes

A one-pot transformation, which involves the reaction of ketones with aldehydes in the presence of metal halides to furnish tetrahydro-2H-pyran-2,4-diols in a highly diastereoselective manner, is investigated thoroughly by experiments and computations. Th

Highly active, water-compatible and easily separable magnetic mesoporous Lewis acid catalyst for the Mukaiyama-Aldol reaction in water

A novel magnetic mesoporous Lewis acid catalyst was prepared through immobilizing Yb(OTf)3 on a sodium propylsulphonate and phenyl group co-functionalized magnetic core-mesoporous silica shell composite. The obtained Yb(OTf)2-SO3Na&Ph-MCMSS catalyst had a typical core-shell structure with a Fe3O4 magnetic core, a middle amorphous silica layer and a multifunctional mesoporous silica shell with radial pore channels. In water medium Mukaiyama-Aldol reactions, it exhibited a higher catalytic reactivity than that of the homogeneous catalyst Yb(OTf)3, and control catalysts Yb(OTf)2-SO3Na-MCMSS without phenyl groups inside the mesoporous channels, Yb(OTf)2-SO 3Na&Ph-MCSS without a mesoporous structure, mesoporous Yb(OTf)2-SO3Na&Ph-MCM-41 with an irregular morphology and nonporous Yb(OTf)2-SO3Na-Amberlyst-15 ion-exchange resin. The systematic analysis demonstrated that this excellent catalytic performance could be attributed to the synergetic effect resulting from its radial mesoporous channels and the pore surface hydrophobicity, leading to the increased accessibility of actives sites and the decreased diffusion limitation of reactants. More importantly, this catalyst was stable in water and could be easily separated with a simple magnet and reused at least six times without loss of catalytic activity. This journal is the Partner Organisations 2014.

Synthesis, spectroscopic characterization, and reactivity of water-tolerant Eu3+-based precatalysts

We report the synthesis, spectroscopic characterization, and reactivity of Eu3+ in the presence of a new set of chiral ligands designed for the aqueous, enantioselective Mukaiyama aldol reaction. Luminescence and NMR measurements were used to characterize the coordination environments of the Eu3+-based precatalysts, and this data is compared with yields and stereoselectivities. In addition to structure-function relationships, we found that, in the presence of excess hexadentate ligands, Eu3+ is coordinatively saturated, and subsequently, the reactivity of the precatalysts is reduced. These findings are helpful for the design of new ligands that bind Eu3+ without saturating the Eu3+ coordination sphere.

An extremely stable and highly active periodic mesoporous Lewis acid catalyst in water-medium Mukaiyama-aldol reaction

A periodic mesoporous Lewis acid catalyst ((OTf)2Sc-SO 3-Ph-PMO) was synthesized through chelating scandium triflate (Sc(OTf)3) with sodium benzenesulfonate-functionalized periodic mesoporous silica (PhSO3Na-Ph-PMO). Compared with homogeneous catalyst Sc(OTf)3 and mesoporous SBA-15-supported scandium triflate catalyst ((OTf)2Sc-SO3-Ph-SBA-15), it exhibited superior catalytic activity and selectivity in water-medium Mukaiyama-aldol reaction. Hydrophobicity tests and substrate adsorption experiments demonstrated that its unique catalytic performance was related to the combined advantage of mesoporosity and hydrophobic microenvironment, which effectively stabilized and concentrated the substances as well as decreased intrinsic mass transfer resistance. Noted that the periodically arranged Lewis acids in the mesoporous silica framework inhibited the active sites leaching, leading to its high catalytic recyclability with almost unchanged catalytic efficiency for more than 10 times in water media.

Tetranuclear hafnium(IV) and zirconium(IV) cationic complexes sandwiched between Two Di-Lacunary species of α-keggin polyoxometalates: Lewis acid catalysis of the mukaiyamaaldol reaction

The syntheses, X-ray structures, and homogeneous Lewis acid catalytic activities for the Mukaiyamaaldol reaction of four tetranuclear HfIV and ZrIV cluster cations, which are sandwiched between two 1,2-di-lacunary α-Keggin polyoxomet