149495-00-1

Upstream product

• 75-52-5 nitromethane 
• 100-52-7 benzaldehyde 
• 64-17-5 ethanol 
• 134-81-6 benzil 
• 100-42-5 styrene 
• 17510-46-2 3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene 
• 614-21-1 2-nitroacetophenone 
• 96-09-3 styrene oxide 
• 557-20-0 diethylzinc 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 563-70-2 bromonitromethane 
• 10102-44-0 Nitrogen dioxide 
• 51146-35-1 trimethylsilyl ester of aci-nitromethane 
• 100-51-6 benzyl alcohol 

Downstream Products

• 102-96-5 (2-nitroethenyl)benzene 
• 93682-06-5 2-hydroxyamino-1-phenyl-ethanol; oxalate 
• 7568-93-6 2-Amino-1-phenylethanol 
• 614-21-1 2-nitroacetophenone 
• 5153-67-3 nitrostyrene 
• 444144-86-9 1-(4-chlorophenyl)-2-nitro-1-phenylethane 
• 6125-24-2 2-Phenylnitroethane 
• 4397-12-0 2-hydroxylamine-1-phenylethanol 
• 155112-29-1 1-Nitro-2-phenyl-2-<(trimethylsilyl)oxy>-1-ethane 
• 7732-18-5 water 
• 611-71-2 MANDELIC ACID 
• 611-73-4 Benzoylformic acid 
• 145920-96-3 (R)-2-nitro-1-phenylethanol 
• 38257-72-6 2-fluoro-2-nitro-1-phenyl-ethanol 

Relevant academic research and scientific papers

Heterogeneous chiral copper complexes of amino alcohol for asymmetric nitroaldol reaction

Figure presented. Chiral amino alcohols supported on mesoporous silicas were synthesized and evaluated as a new class of chiral ligands in copper-catalyzed nitroaldol reaction under heterogeneous and mild reaction conditions. The activity and enantioselec

C2 symmetric copper (II) complexes of L-valine and L-phenyl alanine based chiral diimines for catalytic asymmetric Henry reaction

New C2 symmetric chiral diimines were synthesized from the amino acids L-valine and L-phenyl alanine. In situ copper (II) complexes of the chiral diimine ligands were found to catalyze asymmetric Henry reaction. The chiral nitro aldols were formed in excellent yield (99%) and ee (99%). The synthetic utility of the chiral catalysts were screened with various substituted prochiral aromatic and heteroaromatic aldehydes. Possible catalytic cycle for the chiral diimine copper complex catalyzed asymmetric Henry reaction has been proposed. The stereoselectivity of the asymmetric Henry reaction was discussed based on the transition state in the catalytic cycle.

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

A biocatalytic Henry reaction - The hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions

(Figure Presented) Novel enzyme activity: Biocatalytic Henry reactions with nitromethane and nitroethane yielded the corresponding nitroalcohols with good enantio- and diastereo-control in the presence of the hydroxynitrile lyase from the tropical rubber tree Hevea brasiliensis. Molecular modeling and deuterated starting materials were used in mechanistic investigations.

Copper complexes bearing methylthiophenyl and methylfuranyl derivatives of (R,R)-1,2-diaminocyclohexane: X-ray structures and catalytic exploitation in Henry reaction

Abstract Two novel dichloro Cu(II) complexes of (R,R)-N1,N2-bis((5-methylthiophen-2-yl)methyl)cyclohexane-1,2-diamine (MTCHD) and (R,R)-N1,N2-bis((5-methylfuran-2-yl)methyl)cyclohexane-1,2-diamine (MFCHD) ligand

Evaluation of 5-cis-Substituted Prolinamines as Ligands in Enantioselective, Copper-Catalyzed Henry Reactions

The development of a new catalytic system for enantioselective Henry reactions, which permits superb 99 % ee with a broad variety of aldehydes, is presented. In-depth structure-selectivity investigations with 33 5-cis-substituted prolinamines, prepared fr

Revisit to Henry reaction by non conventional heterogeneous and efficient catalyst for nitroalcohol synthesis

A sustainable, green and efficient process for the synthesis of 2-nitro alcohol derivatives from different substituted aromatic aldehydes with nitroalkane by stirring at ambient temperature with high product yield is reported. Adoption of very mild reaction conditions, use of Calcined Eggshell (CES) as natural catalyst and simple workup are expected to contribute to the development of environmentally benign synthetic method for Henry (nitroaldol) reaction. CES is ecologically safe, inexpensive, and attractive heterogeneous base catalyst obtained from renewable resources, thus opening a new perspective for this process. Graphical abstract: [Figure not available: see fulltext.]

One-Pot Enzyme Cascade Catalyzed Asymmetrization of Primary Alcohols: Synthesis of Enantiocomplementary Chiral β-Nitroalcohols

Biocatalytic asymmetrization of inexpensive and stable primary alcohols to prepare enantioenriched β-nitroalcohols is an important development in green chemistry for the production of chiral pharmaceutical intermediates. Herein, we report a one-pot, two-step cascade reaction sequence in which first benzylic alcohols were oxidized to produce corresponding benzaldehydes using horse liver alcohol dehydrogenase (HLADH). The in situ generated aldehydes were then reacted in a biphasic medium with nitromethane by Arabidopsis thaliana hydroxynitrile lyase (AtHNL) or Baliospermum montanum HNL (BmHNL) catalyzed Henry reaction to produce stereoselective β-nitroalcohols with (R) or (S) configuration, respectively. Using HLADH-AtHNL, (R)-β-nitroalcohols were obtained in up to 64% conversion, and HLADH-BmHNL, (S)-β-nitroalcohols in up to 70% conversion, while in both cases excellent stereoselectivity (up to >99% ee) was achieved. The concept was proven by functionalization of sp3 C?H bond of ten simple achiral benzylic alcohols to enantiocomplementary chiral β-nitroalcohols. (Figure presented.).

High performance of ultrasonic-assisted synthesis of two spherical polymers for enantioselective catalysis

Chiral polymers have aroused great attention in among chiral supramolecular materials based on their features. Herein, for the first time, the synthesis of chiral polymeric composites (CMNPs/1,4-Zbtb & 1,3-Zbtb) have been reported with entrapment through

(3S,4S)-N-substituted-3,4-dihydroxypyrrolidines as ligands for the enantioselective Henry reaction

The enantioselective Henry reaction is a very important and useful carbon–carbon bond forming reaction. The execution of this reaction requires the use of efficient chiral catalysts. In this work, in situ formed complexes of N-substituted dihydroxypyrrolidines, chiral ligands derived from L-tartaric acid and amines, were evaluated as catalysts in the enantioselective Henry reaction. The results showed that the nature of the N-substituent on the ligand significantly influences the outcome of the reaction. Best results were obtained using a Cu (II) complex of (3S,4S)-N-benzyl-3,4-dihydroxypyrrolidine, in the presence of DIPEA, for the reaction of aromatic aldehydes with nitromethane, at room temperature, originating products with er up to 92:8 (R:S) and conversions up to 96%. The interaction between the pyrrolidine ligand and the copper ion, in isopropanol, was followed by UV-vis spectrophotometry, showing a 1:1 stoichiometry and a binding constant of 4.4. The results obtained will contribute to the design and development of more efficient chiral catalysts for this type of reaction.