93643-64-2

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 116-11-0 2-Methoxypropene 
• 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 
• 58547-18-5 6-phenyl-4-hydroxyhexan-2-one 
• 1402010-09-6 (4S,5S)-2-((R)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane 
• 66536-78-5 (+)-(R)-1-(p-tolylsulfinyl)-2-propanone 

Relevant academic research and scientific papers

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

Application of Allylzinc Reagents as Nucleophiles in Matteson Homologations

Allylzinc reagents are versatile nucleophiles that can be used in Matteson homologations. The linear substitution products are formed almost exclusively, and excellent E selectivities are observed in reactions of reagents with sterically demanding or aryl

Emergence of a catalytic tetrad during evolution of a highly active artificial aldolase

Designing catalysts that achieve the rates and selectivities of natural enzymes is a long-standing goal in protein chemistry. Here, we show that an ultrahigh-throughput droplet-based microfluidic screening platform can be used to improve a previously optimized artificial aldolase by an additional factor of 30 to give a >10 9 rate enhancement that rivals the efficiency of class I aldolases. The resulting enzyme catalyses a reversible aldol reaction with high stereoselectivity and tolerates a broad range of substrates. Biochemical and structural studies show that catalysis depends on a Lys-Tyr-Asn-Tyr tetrad that emerged adjacent to a computationally designed hydrophobic pocket during directed evolution. This constellation of residues is poised to activate the substrate by Schiff base formation, promote mechanistically important proton transfers and stabilize multiple transition states along a complex reaction coordinate. The emergence of such a sophisticated catalytic centre shows that there is nothing magical about the catalytic activities or mechanisms of naturally occurring enzymes, or the evolutionary process that gave rise to them.

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.

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.

Highly enantioselective biomimetic intramolecular dehydration: Kinetic resolution of β-hydroxy ketones catalyzed by β-turn tetrapeptides

Racemic β-hydroxy ketones were kinetically resoluted into the enantiopure isomers and (E)-α,β-unsaturated ketones using catalytic asymmetric intramolecular dehydration for the first time. Synthetic tetrapeptides were used to imitate fatty acid dehydratase

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

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

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%).