155189-76-7

Upstream product

• 50-00-0 formaldehyd 
• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 657394-58-6 (R)-3-(tert-butyldimethylsilyloxy)-2-methyl-1-phenylpropan-1-one 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 93-55-0 1-phenyl-propan-1-one 
• 1309881-44-4 (S)-(-)-(Z)-4-[4-acetyl-1-(4-bromobenzenesulfonyl)-2,5-dihydro-1H-pyrrol-3-yl]-2-methyl-3-phenylpent-3-enoic acid ethyl ester 
• 1309881-88-6 C₂₄H₂₈BrNO₄S 
• 1309881-89-7 C₃₆H₅₆BrNO₄SSi₂ 
• 16735-22-1 3-hydroxy-2-methylpropiophenone 
• 100-52-7 benzaldehyde 
• 10488-87-6 ethyl 2-benzoylpropionate 

Downstream Products

• 127379-92-4 (1S,2R)-2-methyl-1-phenyl-propane-1,3-diol 
• 139068-60-3 (2R,3R)-2-methyl-3-phenyl-1,3-propane diol 

Relevant academic research and scientific papers

Lewis acid-catalyzed asymmetric hydroxymethylation of silicon enolates in aqueous media

Asymmetric hydroxymethylation of silicon enolates with formaldehyde in aqueous media has been achieved using praseodymium triflate and a chiral crown ether. Formaldehyde aqueous solution can be directly used for the reactions, and a water/THF mixture was found to be the best solvent system. This is the first example of catalytic asymmetric hydroxymethylation of silicon enolates.

Bismuth triflate-chiral bipyridine complexes as water-compatible chiral lewis acids

(Chemical Equation Presented) Catalytic asymmetric hydroxymethylation of silicon enolates with an aqueous formaldehyde solution has been developed using a chiral bismuth complex. This is the first example of highly enantioselective reactions using a chira

Catalytic asymmetric hydroxymethylation of silicon enolates using an aqueous solution of formaldehyde with a chiral scandium complex

Catalytic asymmetric hydroxymethylation of silicon enolates has been achieved. In this reaction, an aqueous solution of formaldehyde can be used to realize an easy and safe procedure, and high enantioselectivities have been obtained. This is the first exa

Chiral scandium-catalyzed enantioselective hydroxymethylation of ketones in water

Scandium-catalyzed enantioselective hydroxymethylation of ketones has been developed using aqueous formaldehyde (formalin) in water. The addition of a catalytic amount of pyridine enables the use of ketones directly in asymmetric hydroxymethylation reactions. (Chemical equation presented).

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.).

Toward chemistry-based design of the simplest metalloenzyme-like catalyst that works efficiently in water

Enzymes exhibit overwhelmingly superior catalysis compared with artificial catalysts. Current strategies to rival enzymatic catalysis require unmodified or minimally modified structures of active sites, gigantic molecular weight, and sometimes the use of harsh conditions such as extremely low temperatures in organic solvents. Herein, we describe a design of small molecules that act as the simplest metalloenzyme-like catalysts that can function in water, without mimicking enzyme structures. These artificial catalysts efficiently promoted enantioselective directtype aldol reactions using aqueous formaldehyde. The reactions followed Michaelis-Menten kinetics, and heat-resistant asymmetric environments were constructed in water.

Rhodium-catalyzed asymmetric formal olefination or cycloaddition: 1,3-dicarbonyl compounds reacting with 1,6-diynes or 1,6-enynes

A cationic rhodium(I) complex catalyzes the title reaction of 1,6-diynes through a [2+2+2] cycloaddition and subsequent electrocyclic ring opening (see scheme; cod=1,5-cyclooctadiene, H8-binap=2,2′- bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1, 1′-binaphthyl). The asymmetric intramolecular [2+2+2] cycloaddition of 1,3-dicarbonyl compounds with 1,6-enynes was also accomplished. Copyright

Enantioselective evans-tishchenko reduction of β-hydroxyketone catalyzed by lithium binaphtholate

Lithium diphenylbinaphtholate catalyzed the enantioselective Evans-Tishchenko reduction of achiral β-hydroxyketones to afford monoacyl-protected 1,3-diols with high stereoselectivities. In the reaction of racemic β-hydroxyketones, kinetic optical resolution occurred in a highly stereoselective manner.

Lewis acid catalysis in water with a hydrophilic substrate: Scandium-catalyzed hydroxymethylation with aqueous formaldehyde in water

(Chemical Equation Presented) Synthesis in deep water: For the title reaction, which proceeds with high selectivities, acid-base interactions between the Sc catalyst and HCHO are important. The reaction was used in the synthesis of an odorant to demonstra

A heterogeneous silica-supported scandium/ionic liquid catalyst system for organic reactions in water

(Figure Presented) Several carbon-carbon bond-forming reactions are catalyzed by a silica-supported scandium triflate catalyst combined with an ionic liquid. The combination of these two components creates a hydrophobic reaction environment in water (see scheme; blue: water, yellow: substrate, orange: ionic liquid).