610758-06-0

Upstream product

• 75-52-5 nitromethane 
• 135-02-4 ortho-anisaldehyde 
• 46270-50-2 1-(2-methoxyphenyl)-2-nitroethan-1-one 
• 579-75-9 2-Methoxybenzoic acid 

Downstream Products

• 54942-63-1 (R)-2-Amino-1-(2-methoxy-phenyl)-ethanol 

Relevant academic research and scientific papers

Enantioselective copper(II)-catalyzed Henry reaction utilizing chiral aziridinyl alcohols

A family of enantiopure β-aminoalcohols based on aziridine backbones were synthesized, and examined as chiral ligands for the copper(II)-catalyzed asymmetric Henry reaction of aromatic aldehydes with nitromethane, giving β-nitroalcohols in excellent yield

Polystyrene copolymer supported by substituted (1R,2R)-1,2-diphenylethane- 1,2-diamine-copper(II) complexes: A recyclable catalyst for asymmetric Henry reactions Dedicated to Professor Vladimír Machá?ek on the occasion of his 70th birthday

Herein described the preparation of swelling pearl-like copolymer styrene - 4-vinylbenzyl chloride cross-linked by means of tetra(ethylene glycol)-bis(4-vinylbenzyl)ether (200-800 μm). The pearl-like polymer was used to anchor (1R,2R)-1-amino-2-(2,3-dihyd

Henry reaction catalyzed by new series of imidazolidine-4-one Cu-complexes

A series of 5-tert-butyl-2-(pyridine-2-yl)imidazolidine-4-ones have been prepared and their Cu(II) complexes studied as enantioselective catalysts of the asymmetric Henry reaction of various aldehydes with nitromethane. It was found that these compounds w

Synthesis of novel Schiff base ligands from gluco- and galactochloraloses for the Cu(II) catalyzed asymmetric Henry reaction

A series of chiral Schiff base ligands has been prepared using aminochloralose derivatives of glucose and galactose. These ligands were used as catalysts in the asymmetric Henry reaction in the presence of Cu(II) ions giving yields of up to 95%. An intere

(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.

Asymmetric Cu-catalyzed Henry reaction using chiral camphor Schiff bases immobilized on a macromolecular chain

Immobilized catalysts have attracted chemists’ attention for long time because of convenient recycling, which is very important for some special catalyst even immobilizations accompanying the decrease of catalytic activity and selectivity. Our group focus

Cu(II)-L-prolinamide: First catalytic application of metal-amidoamine complex in enantioselective Henry reaction

For asymmetric Henry reaction, catalysis by chiral metal complexes is often prefered over aminocatalysis. Despite using many complicated L-proline derived ligands, the use of L-prolinamides as ligand in metal catalyzed Henry reaction is conspicuously abse

Isosteric expansion of the structural diversity of chiral ligands: Design and application of proline-based N,N′-dioxide ligands for copper-catalyzed enantioselective Henry reactions

Chiral N,N′-dioxide catalysts were designed based on isosteric approach. Using L-Proline as the starting material, a variety of chiral N,N′-dioxide ligands were obtained via conventional functional group transformations and were utilized in asymmetric Henry reactions between nitromethane and aromatic aldehydes. Using the N,N′-dioxide-copper(II) complexes as the catalysts, asymmetric Henry reaction produced the corresponding β-nitroalcohols in up to 66% yields and up to 83% ee's under mild conditions. The reactions were easy to carry out, and special care such as air or moisture-free conditions was not required.

Ketoreductase catalyzed stereoselective bioreduction of α-nitro ketones

We report here the stereoselective bioreduction of α-nitro ketones catalyzed by ketoreductases (KREDs) with publicly known sequences. YGL039w and RasADH/SyADH were able to reduce 23 class I substrates (1-aryl-2-nitro-1-ethanone (1)) and ten class II substrates (1-aryloxy-3-nitro-2-propanone (4)) to furnish both enantiomers of the corresponding β-nitro alcohols, with good-to-excellent conversions (up to >99%) and enantioselectivities (up to >99% ee) being achieved in most cases. To the best of our knowledge, KRED-mediated reduction of class II α-nitro ketones (1-aryloxy-3-nitro-2-propanone (4)) is unprecedented. Select β-nitro alcohols, including the synthetic intermediates of bioactive molecules (R)-tembamide, (S)-tembamide, (S)-moprolol, (S)-toliprolol and (S)-propanolol, were stereoselectively synthesized in preparative scale with 42% to 90% isolated yields, showcasing the practical potential of our developed system in organic synthesis. Finally, the advantage of using KREDs with known sequence was demonstrated by whole-cell catalysis, in which β-nitro alcohol (R)-2k, the key synthetic intermediate of hypoglycemic natural product (R)-tembamide, was produced in a space-time yield of 178 g L?1 d?1 as well as 95% ee by employing the whole cells of a recombinant E. coli strain coexpressing RasADH and glucose dehydrogenase as the biocatalyst.

Enhanced Activity and Enantioselectivity of Henry Reaction by the Postsynthetic Reduction Modification for a Chiral Cu(salen)-Based Metal-Organic Framework

Metal-organic frameworks (MOFs) imbedded privileged molecular catalysts are of particular interest due to their higher catalytic activities derived from the MOFs pore/channel confinement effect, improved lifetime through eliminating intermolecular deactiv