1335017-70-3

Upstream product

• 75-52-5 nitromethane 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 14438-63-2 1-(2,5-dimethoxyphenyl)-2-nitroethanol 

Relevant academic research and scientific papers

Production of (S)-β-Nitro Alcohols by Enantioselective C?C Bond Cleavage with an R-Selective Hydroxynitrile Lyase

Hydroxynitrile lyase (HNL)-catalysed stereoselective synthesis of β-nitro alcohols from aldehydes and nitroalkanes is considered an efficient biocatalytic approach. However, only one S-selective HNL—Hevea brasiliensis (HbHNL)—exists that is appropriate for the synthesis of (S)-β-nitro alcohols from the corresponding aldehydes. Further, synthesis catalysed by HbHNL is limited by low specific activity and moderate yields. We have prepared a number of (S)-β-nitro alcohols, by kinetic resolution with the aid of an R-selective HNL from Arabidopsis thaliana (AtHNL). Optimization of the reaction conditions for AtHNL-catalysed stereoselective C?C bond cleavage of racemic 2-nitro-1-phenylethanol (NPE) produced (S)-NPE (together with benzaldehyde and nitromethane, largely from the R enantiomer) in up to 99 % ee and with 47 % conversion. This is the fastest HNL-catalysed route known so far for the synthesis of a series of (S)-β-nitro alcohols. This approach widens the application of AtHNL for the synthesis not only of (R)- but also of (S)-β-nitro alcohols from the appropriate substrates. Without the need for the discovery of a new enzyme, but rather by use of a retro-Henry approach, it was used to generate a number of (S)-β-nitro alcohols by taking advantage of the substrate selectivity of AtHNL.

Asymmetric henry reaction catalyzed by chiral schiff base

Four chiral Schiff bases were synthesized conveniently from chiral amino alcohol and 2-hydroxynaphthalene-1-carbaldehyde. These ligands were used to catalyze the addition of nitroalkanes to aldehydes under ambient conditions in good yields with up to 91%

Asymmetric Henry reaction catalyzed by Cu(I)-based chiral amino alcohol complex

The Cu(I)-based complex prepared from (S)-2-(furan-2-yl-methylamino)-2- phenylethanol (5c) and CuCl was used as catalyst in enantioselective Henry reactions of arylaldehydes and nitromethane, which gave 89% ee and 95% yield at ambient temperature. The proposed catalytic cycle of an asymmetric Henry reaction was suggested. TUeBITAK.

Enantioselective Henry reaction catalyzed by a copper(II) glucoBOX complex

A highly enantioselective Henry reaction has been developed using a chiral copper(II)-glucoBOX complex. The catalytic system works well with a wide range of aromatic, aliphatic and heteroaromatic aldehydes to afford the corresponding nitroalkanols with hi