868151-97-7

Upstream product

• 75-52-5 nitromethane 
• 529-20-4 2-methylphenyl aldehyde 
• 71315-64-5 2-nitro-1-(o-tolyl)ethan-1-one 
• 933-88-0 ortho-toluoyl chloride 
• 3991-75-1 N-(2-methylbenzoyl)imidazole 

Downstream Products

• 133562-34-2 (S)-2-Amino-1-o-tolyl-ethanol 

Relevant academic research and scientific papers

Synthesis of Chiral Tetrahydroisoquinoline and C 2-Symmetric Bistetrahydroisoquinoline Ligands and Their Application in the Enantioselective Henry Reaction

Application of chiral tetrahydroisoquinoline and bistetrahydroisoquinoline scaffolds in asymmetric reactions is limited by the inefficient synthesis of their chiral structural variants. We have conveniently synthesized 24 such variants and applied them as

(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.

Synthesis of chiral salan ligands with bulky substituents and their application in Cu-catalyzed asymmetric Henry reaction

Several new chiral N,N’-dimethylated salan ligands with bulky substituents were synthesized and their in-situ generated Cu(II) complexes were evaluated in the asymmetric Henry reaction. Substituents on the aryloxide moieties of these ligands were found to

Method for water-phase catalysis of Henry asymmetric addition reaction based on polyion liquid type chiral amino acid copper catalyst

The invention relates to the field of asymmetric catalysis, in particular to a method for water-phase catalysis of a Henry asymmetric addition reaction through a polyion liquid type chiral amino acidcopper catalyst. In a water phase, an aldehyde compound

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.

A new type of L-Tertiary leucine-derived ligand: Synthesis and application in Cu(II)-catalyzed asymmetric Henry reactions

A new series of Schiff bases derived from amino acids were developed as chiral ligands for Cu(II)-catalyzed asymmetric Henry reactions. The optimum ligand 7d exhibited outstanding catalytic efficiency in the Cu(II)-catalyzed asymmetric Henry additions of four nitroalkanes to different kinds of aldehydes to produce 76 desired adducts in high yields (up to 96%) with excellent enantioselectivities, up to 99% enantiomeric excess (ee).

Levopimaric acid derived 1,2-diamines and their application in the copper-catalyzed asymmetric Henry reaction

Levopimaric acid, a readily available starting material, was used in efficient syntheses of new enantiopure diamines and Schiff bases with good yields. The synthetic procedure is based on the fumaropimaric acid monomethyl ester conversion into the optical

Synthesis of chiral salalen ligands and their in-situ generated Cu-complexes for asymmetric Henry reaction

Chiral salalen ligands derived from (S)-proline and derivatives of salicyaldehydes were synthesized, and their in-situ generated Cu (II) complexes were evaluated in the asymmetric Henry reaction. Salalen ligand of different substituents on the phenyl moiety showed remarkable effect on the enantioselectivity of nitro-aldol product of 4-nitrobenzaldehyde and nitromethane. Cu (II) complex generated in situ with (S)-2-(tert-butyl)-6-((2-(((2-hydroxy-3-methylbenzylidene)amino)methyl)pyrrolidin-1-yl)methyl) phenol (10?mol%) and Cu (OAc)2.H2O (10?mol%), found to be better catalyst for nitro-aldol reaction between 4-nitrobenzaldehyde and nitromethane, gave corresponding product in 85% yield and 88% enantiomeric excess (ee) in isopropanol at 35°C after 40?hours. The catalyst also used for the Henry reaction with different substituted benzaldehydes and corresponding products were obtained in 22% to 99% yields with 66% to 92% ee. Henry reaction of 4-nitrobenzaldehyde and prochiral nitroethane gave anti-selective product (dr?=?79/21; anti/syn) in a 91% yield with 80% ee.

Asymmetric Henry reaction catalyzed by chiral Cu(II) salalen and salan complexes derived from (S)-proline

Single chiral center C1 symmetric salalen and salan ligands were synthesized from (S)-proline and their Cu(II) complexes were used as catalysts for the asymmetric Henry reaction between aromatic aldehydes and nitromethane/nitroethane. The react

The synthesis of chiral tridentate ligands from L-proline and their application in the copper(II)-catalyzed enantioselective Henry reaction

A series of chiral tridentate ligands derived from readily available enantiopure L-proline were designed and synthesized. The ligands together with Cu(OAc)2 were successfully used in asymmetric Henry reactions. Various structurally divergent aldehydes and nitromethane were converted into versatile β-nitro alcohols in MeOH at room temperature with very good yields (up to 85%) and enantioselectivities (up to 86%).