29865-56-3

Upstream product

• 155988-36-6 (E)-1-chloro-3-(2-nitroprop-1-en-1-yl)benzene 
• 587-04-2 m-Chlorobenzaldehyde 
• 19394-34-4 (E)-1-(3'-chlorophenyl)-2-nitropropene 

Relevant academic research and scientific papers

The organic-synthetic potential of recombinant Ene reductases: Substrate-Scope Evaluation and Process Optimization

In this study an evaluation of the synthetic potential of a broad range of recombinant ene reductases was performed. In detail, a library of 23 ene reductases was used to screen the C=C reduction of 21 activated alkenes from different compound classes as substrates. The chosen set of substrates comprises nitroalkenes with an aryl substituent at the β-position and a methyl substituent at the α- or β-position, α,β-unsaturated carboxylic acids and their esters with and without substituents at the β-position, a range of cyclic α,β-unsaturated ketones with different ring sizes and substitution patterns and one α,β-unsaturated boronic acid. After we obtained insight into the substrate scope, several biotransformations were prioritised and further investigated in a screening of 41 reaction parameters (which included chaotropic and kosmotropic salts, polyols, buffer solutions, amino acids and organic solvents) towards their impact on the activity and enantioselectivity of the applied ene reductases. Under the optimised conditions, selected reduction processes were performed on an increased lab scale (up to 30 mL) with up to 10% substrate concentration, which led in general to both high conversion and (if chiral products were formed) enantioselectivity. Comprehensive screening: A detailed screening of 23 recombinant ene reductases for the reduction of 21 activated alkenes is performed as well as a subsequent study of the influence of 41 reaction parameters towards the enzyme activity and selectivity of selected reactions. In addition, a range of biocatalytic reductions on an increased laboratory scale are performed with substrate concentrations between 5 and 100 gL-1. EWG=Electron-withdrawing group.

Enantioselective hydrogenation of α,β-disubstituted nitroalkenes

The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.

The highly chemoselective transfer hydrogenation of the carbon-carbon double bond of conjugated nitroalkenes by a rhodium complex

Chemoselective transfer hydrogenation of conjugated nitroalkenes catalyzed by [RhCl2Cp·]2-diamine complex (Cp ·=η5-C5Me5) using HCOOH/Et3N (5:2) (TEAF) as a hydrogen source was realized. A variety of nitrostyrenes, β-methyl nitrostyrenes, and 3-methyl-4-nitro-5-alkenyl- isoxazoles were reduced smoothly in good to excellent yields in short reaction time. Other functional groups are inert under the reaction conditions.

Asymmetric reduction of nitroalkenes with baker's yeast

Various α,β-disubstituted and trisubstituted nitroalkenes were chemoselectively reduced with baker's yeast to the corresponding nitroalkanes. Stereoselectivities of the reduction of α,β-disubstituted nitroalkenes were modest to low, and e.e.s up to 52% were obtained. Trisubstituted nitroalkenes could be reduced to the corresponding nitroalkanes with excellent enantioselectivities, moderate diastereoselectivities and in good yield.

REDUCTION OF AROMATIC NITROALKENES WITH BAKER'S YEAST

Aromatic nitroalkenes were reduced chemoselectively with baker's yeast to give the corresponding nitroalkanes.