255841-10-2

Upstream product

• 21667-60-7 3-methoxybenzoylacetonitrile 
• 591-31-1 3-methoxy-benzaldehyde 
• 75-05-8 acetonitrile 
• 5000-65-7 2-bromo-3'-methoxyacetophenone 
• 103205-23-8 3-hjydroxy-3-(3-methoxyphenyl)propanenitrile 

Relevant academic research and scientific papers

Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel–Carbene Complexes

A direct catalytic asymmetric addition of acetonitrile to aldehydes that realizes over 90 % ee is the ultimate challenge in alkylnitrile addition chemistry. Herein, we report achieving high enantioselectivity by the strategic use of a sterically demanding NiII pincer carbene complex, which afforded highly enantioenriched β-hydroxynitriles. This highly atom-economical process paves the way for exploiting inexpensive acetonitrile as a promising C2 building block in a practical synthetic toolbox for asymmetric catalysis.

Imidazolium-based organoiridium-functionalized periodic mesoporous organosilica boosts enantioselective reduction of α-cyanoacetophenones, α-nitroacetophenones, and β-ketoesters

An imidazolium-based, organoiridium-functionalized periodic mesoporous organosilica is developed through complexation of chiral pentafluorophenylsulfonyl-1,2-diphenylethylenediamine and organoiridiumfunctionalized periodic mesoporous organosilica. Structural analyses and characterizations of catalyst reveal well-defined single-site iridium active species within its organosilicate network. Electron microscopy confirms a highly ordered dimensional-hexagonal mesostructure. This bifunctional heterogeneous catalyst displays excellent catalytic performance in the enantioselective reduction of α-cyano and α-nitroacetophenones. As expected, incorporation of imidazolium-functionality within hydrophobic periodic mesoporous organosilica promotes catalytic activity and enantioselectivity. In addition, this heterogeneous catalyst can be recovered and reused for at least eight times without loss of its catalytic activity. Furthermore, the approach described here can also construct another organoiridium-functionalized periodic mesoporous organosilica through postcoordination of chiral methylsulfonyl-1,2-diphenylethylenediamine, which provides excellent catalytic activity and enantioselectivity in the enantioselective reduction of β-ketoesters. The method presented here offers a potential way for immobilizing various chiral ligands to construct chiral organometal-functionalized periodic mesoporous organosilicas.

Imidazolium-based organoiridium-functionalized periodic mesoporous organosilica boosts enantioselective reduction of α-cyanoacetophenones, α-nitroacetophenones, and β-ketoesters

An imidazolium-based, organoiridium-functionalized periodic mesoporous organosilica is developed through complexation of chiral pentafluorophenylsulfonyl-1,2-diphenylethylenediamine and organoiridium-functionalized periodic mesoporous organosilica. Structural analyses and characterizations of catalyst reveal well-defined single-site iridium active species within its organosilicate network. Electron microscopy confirms a highly ordered dimensional-hexagonal mesostructure. This bifunctional heterogeneous catalyst displays excellent catalytic performance in the enantioselective reduction of α-cyano and α-nitroacetophenones. As expected, incorporation of imidazolium-functionality within hydrophobic periodic mesoporous organosilica promotes catalytic activity and enantioselectivity. In addition, this heterogeneous catalyst can be recovered and reused for at least eight times without loss of its catalytic activity. Furthermore, the approach described here can also construct another organoiridium-functionalized periodic mesoporous organosilica through postcoordination of chiral methylsulfonyl-1,2-diphenylethylenediamine, which provides excellent catalytic activity and enantioselectivity in the enantioselective reduction of β-ketoesters. The method presented here offers a potential way for immobilizing various chiral ligands to construct chiral organometal-functionalized periodic mesoporous organosilicas.

Stereocomplementary bioreduction of β-ketonitrile without ethylated byproduct

α-Ethylation is competing with the biocatalytic reduction of aromatic β-ketonitriles in a whole-cell system. Use of two newly mined robust and stereocomplementary carbonyl reductases in a biphasic system has completely eliminated the competing byproduct.

Enantioselective reduction of α-Cyano and α-Nitro substituted acetophenones promoted by a bifunctional mesoporous silica

Pores that put your reaction in a spin! A recoverable mesoporous silica exhibits excellent catalytic activity and enhanced enantioselectivity for the reduction of α-cyano and α-cyanoacetophenones that ascribes the synergistic effect of its phase-transfer

Iridium diamine catalyst for the asymmetric transfer hydrogenation of ketones

A simple and very efficient chiral aqua iridium(III) diamine complex leads to excellent enantioselectivities in the asymmetric transfer hydrogenation of various α-cyano and α-nitro ketones. The catalyst provides the ortho-substituted aromatic alcohols with especially high ee values. The diamine ligands can be used directly as chiral ligands; conversion into the corresponding sulfamide is not necessary.

CHIRAL IRIDIUM AQUA COMPLEX AND METHOD FOR PRODUCING OPTICALLY ACTIVE HYDROXY COMPOUND BY USING THE SAME

The present invention provides a novel chiral iridium aqua complex used for asymmetric transfer hydrogenation. The present invention relates to chiral iridium aqua complex represented by the formula (1): wherein R1 and R2 are the sam

Asymmetric synthesis of both antipodes of β-hydroxy nitriles and β-Hydroxy carboxylic acids via enzymatic reduction or sequential reduction/hydrolysis

Use of isolated carbonyl reductases in the reduction of aromatic β-ketonitriles have completely eliminated the competing α-ethylation, which is often observed with whole cell biocatalysts. By choosing suitable recombinant carbonyl reductase, the reduction

Unexpected stereorecognition in nitrilase-catalyzed hydrolysis of β-hydroxy nitriles

Biocatalytic enantioselective hydrolysis of β-hydroxy nitriles to corresponding (S)-enriched β-hydroxy carboxylic acids has been achieved for the first time by an isolated nitrilase bII6402 from Bradyrhizobium japonicum USDA110. This offers a new "green" approach to optically pure β-hydroxy nitriles and β-hydroxy carboxylic acids. The observed remote stereorecognition is surprising because this nitrilase shows no enantioselectivity for the hydrolysis of α-hydroxy nitriles such as mandelonitrile.

Chemo- and Stereoselective Reduction of an α-cyanoketone by Bakers' Yeast at Low Temperature

(Matrix Presented) The bakers' yeast mediated reduction of 3-oxo-3-phenylpropanenitrile (1) proceeds at 4 °C to give exclusively (S)-3-hydroxy-3-phenylpropanenitrile (3) in 59% yield. This is in contrast to the corresponding reaction at room temperature w