522629-10-3

Upstream product

• 90712-58-6 5-(p-tolyl)-4,5-dihydroisoxazole 
• 84466-40-0 (+/-)-3-hydroxy-3-(4-methylphenyl)propanenitrile 
• 7391-28-8 p-tolueneacetonitrile 

Relevant academic research and scientific papers

Biocatalytic asymmetric ring-opening of dihydroisoxazoles: a cyanide-free route to complementary enantiomers of β-hydroxy nitriles from olefins

By combination of the cyanide-free synthesis of chiral nitriles and the Kemp elimination reaction catalyzed by aldoxime dehydratases, we herein report a new application of aldoxime dehydratase in the asymmetric ring-opening of 5-sub-4,5-dihydroisoxazoles

Substrate evaluation of rhodococcus erythropolis SET1, a nitrile hydrolysing bacterium, demonstrating dual activity strongly dependent on nitrile sub-structure

Assessment of Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position, acids were the major products obtained, along with recovered nitrile after biotransformation, as a result of suspected nitrilase activity of the isolate. Unexpectedly, amides were found to be the major hydrolysis product when the β-hydroxy nitriles possessed a vinyl group at this position. To probe this behaviour further, additional related substrates were evaluated containing electron-withdrawing groups at the α position, and amide was also observed upon biotransformation in the presence of SET1. Therefore this novel isolate has also demonstrated NHase activity with nitriles that appears to be substrate-dependent.

Facile construction of functionalized periodic mesoporous organosilica for Ir-catalyzed enantioselective reduction of α-cyanoacetophenones and α-nitroacetophenones

A facile method to construct chiral organoiridium-functionalized periodic mesoporous organosilica is developed. The heterogeneous catalyst displays excellent catalytic efficiency in the enantioselective reduction of α-cyanoacetophenones and α-nitroacetoph

Transfer hydrogenation in water: Enantioselective, catalytic reduction of α-cyano and α-nitro substituted acetophenones

Catalytic reduction of α-substituted acetophenones under conditions involving asymmetric transfer hydrogenation in water is described. The reaction is conducted in water and open to air, and formic acid is used as reductant.

Asymmetric reduction of β-ketonitriles with a recombinant carbonyl reductase and enzymatic transformation to optically pure β-hydroxy carboxylic acids

α-Ethylation is concomitant with the reduction of aromatic β-ketonitriles catalyzed by whole-cell biocatalysts. Use of isolated carbonyl reductase has completely eliminated this competing reaction. (R)-β-Hydroxy nitriles were obtained via a reduction cata

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.

Method of manufacturing cyano compounds

A method of manufacturing a cyano compound by reacting a carbonyl compound with a nitrile compound having at least one α-hydrogen atom in the presence of a ligand and a metal compound of formula (III), [in-line-formulae]MX??(III) [/in-line-formulae] where

Enantio- and chemoselective bioreduction of β-keto nitriles by the fungus Curvularia lunata

The use of methanol as cosolvent allows the chemoselective reduction of aromatic β-keto nitriles by the fungus Curvularia lunata CECT 2130, yielding the corresponding (S)-β-hydroxy nitriles in a highly enantioselective way. Copyright (C) 2000 Elsevier Science Ltd.