106353-49-5

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 14583-98-3 1-tributylstannanyl-propan-2-one 
• 67-64-1 acetone 
• 33046-41-2 (E)-6-phenyl-3-hexen-2-one 
• 31874-34-7 (E)-2,4-dimethoxybenzaldehyde oxime 
• 116-11-0 2-Methoxypropene 
• 66536-78-5 (+)-(R)-1-(p-tolylsulfinyl)-2-propanone 

Relevant academic research and scientific papers

Direct asymmetric aldol reactions of acetone using bimetallic zinc catalysts

(Equation presented) The enantioselective aldol reaction using a novel binuclear zinc catalyst of acetone with several aldehydes gave products in good yields (62-89%) with a high level of enantioselectivity (ee = 76-92%).

Silica Jar-with-Lid as Chemo-Enzymatic Nano-Compartment for Enantioselective Synthesis inside Living Cells

Nanodevices, harvesting the power of synthetic catalysts and enzymes to perform enantioselective synthesis inside cell, have never been reported. Here, we synthesized round bottom jar-like silica nanostructures (SiJARs) with a chemo-responsive metal-silic

To probe the origin of activation effect of carboxylic acid and (+)-NLE in tridentated titanium catalyst systems

The activation effect of carboxylic acid and positive nonlinear effect ((+)-NLE) in tridentated titanium catalyst systems for hetero Diels-Alder reaction and aldol-type reactions has been first elucidated on the basis of X-ray crystal structural analysis

Synthesis and characterization of TiL2 complexes with tridentate (ONO) (S)-NOBIN Schiff-base ligands

Tridentate (ONO) C1-symmetric Schiff base ligands were synthesized by the condensation of (S)-2-amino-2′-hydroxy-1,1′-binaphthyalene with 4-hydroxy-3-phenanthrenecarboxaldehyde or 1-hydroxybenz[a]anthracene-2-carboxaldehyde. C2-symmetric titanium(IV) Schiff base complexes, TiL2, were synthesized and characterized with these ligands. The complex with the benz[a]anthryl unit crystallizes in a facial coordination mode, OC-6-1′3′-C, whereas complex with phenanthryl unit crystallizes in a meridional mode, OC-6-22′-A. A comparison between the complexes and the ligands were done in solution using circular dichroism spectroscopy. Preliminary catalytic studies showed that these complexes can catalyze asymmetric carbonyl-ene addition reactions of 2-methoxypropene with aromatic aldehydes with moderate selectivity. The ligands and complexes were characterized by NMR, HRMS, single crystal X-ray diffraction and CD spectroscopy.

Improved conditions for the proline-catalyzed aldol reaction of acetone with aliphatic aldehydes

The proline-catalyzed asymmetric aldol reaction between aliphatic aldehydes and acetone has, to date, remained underdeveloped. Challenges in controlling this reaction include avoiding undesired side reactions such as aldol condensation and self-aldolization. In recent years we have developed optimized conditions, which enable high yields and good to excellent enantioselectivities, and which are presented in this communication. Georg Thieme Verlag Stuttgart New York.

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Catalytic asymmetric hydroperoxidation of α,β-unsaturated ketones: An approach to enantiopure peroxyhemiketals, epoxides, and aldols

(Chemical Equation Presented) Efficient, selective: The primary amine salt 1 derived from quinine efficiently catalyzes the highly enantioselective hydroperoxidation of α,β-unsaturated ketones furnishing stable and isolable cyclic peroxyhemiketals in enan

Organocatalytic asymmetric β-hydroxylation of α,β- unsaturated ketones

The highly enantioselective organocatalytic β-hydroxylation of α,β-unsaturated ketones was accomplished by using oximes as the oxygen-centered nucleophile. Optically active products are obtained with enantioselectivity up to 94 %. Central to these studies was the use of catalytic primary amine salt A, in which both the cation and the anion are chiral. Amine A exhibits high reactivity and selectivity for iminium-ion catalysis with enones. The potential interest of this novel transformation was demonstrated with the easy conversion of the Michael adducts in enantioenriched anti and syn 1,2-diols without erosion of the optical purity. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Efficient asymmetric catalysis of chiral organoaluminum complex for enantioselective ene reactions of aldehydes

Chiral organoaluminum complex 1 efficiently catalyzed the asymmetric hetero-ene reaction of commercially available 2-methoxypropene (2) with aldehydes under mild conditions to give the corresponding β-hydroxymethyl ketones 3 in good to excellent chemical