773148-47-3

Upstream product

• 5153-67-3 nitrostyrene 
• 108-59-8 malonic acid dimethyl ester 
• 75-52-5 nitromethane 
• 100-52-7 benzaldehyde 
• 102-96-5 (2-nitroethenyl)benzene 
• 28868-76-0 2-chlorodimethylmalonate 

Downstream Products

• 71657-88-0 (4R)-4-phenyl-2-pyrrolidone 

Relevant academic research and scientific papers

Cupreine grafted onto silica as an enantioselective and recyclable catalyst for the 1,4-addition of malonate to trans-β-nitrostyrene

Preparation of silica supported cupreine (CPN) and its high catalytic performance for the asymmetric 1,4-addition of dimethyl malonate to trans-β-nitrostyrene in some biomass-derived solvents (2-methyl THF, EtOAc and EtOH) are reported for the first time.

Chiral Tricationic Tris(1,2-diphenylethylenediamine) Cobalt(III) Hydrogen Bond Donor Catalysts with Defined Carbon/Metal Configurations; Matched/Mismatched Effects upon Enantioselectivities with Enantiomeric Chiral Counter Anions

The enantiopure and diastereopure salts λ- or Δ-[Co((S,S)-dpen)3]3+ 2Cl-BArf - (λ- or Δ-(S,S)-13+ 2Cl-BArf - dpen/BArf = 1,2-diphenylethylenediamine/B(3,5-C6H3(CF3)2)4) and λ-(S,S)-13+ 3Cl- are treated with salts of the enantiopure chiral monoanions (A-) or dianions (A2-) 3-bromocamphor-8-sulfonate (camphSO3 -), 1,1′-binaphthyl-2,2′-diyl phosphate (and three 3,3′-disubstituted derivatives), a related biphenanthryl species, tartrate, and Sb2(tart′)2 2- (tart′ = [-O2C-CHO--CHO--CO2 -]). The lipophilic salts λ- or Δ-(S,S)-13+ 2A-BArf -, λ-(S,S)-13+ A2-BArf -, and λ-(S,S)-13+ 3A- are isolated as hydrates and characterized by NMR and microanalyses. In the presence of tertiary amines, many of these are highly enantioselective catalysts for additions of 1,3-dicarbonyl compounds to trans-β-nitrostyrene and di-tert-butylazodicarboxylate. The ee values for diastereomeric salts can exhibit significant differences (avg/high/median Δ%ee = 10/63/6; matched/mismatched effect), and in a few cases, they are better than those obtained with λ- or Δ-(S,S)-13+ 2Cl-BArf -. The crystal structure of Δ-(S,S)-13+ 2(1S)-camphSO3 -BArf - shows that the two sulfonate moieties hydrogen-bond to opposite (idealized) C3-symmetric faces of the trication, with a separate oxygen atom associated with each of the three synperiplanar NH groups.

Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: Inversion of configuration at C9 dramatically improves catalyst performance

(Chemical Equation Presented) Natural not always best: Novel N-aryl urea and thiourea derivatives of dihydrocinchona alkaloids serve as efficient catalysts for the asymmetric addition of dimethyl malonate to a range of nitroalkenes. Catalytic activity and

Lipophilic chiral cobalt (III)complexes of hexaamine ligands: Efficacies as enantioselective hydrogen bond donor catalysts

Four known chiral enantiopure octahedral cobalt(III)trichloride salts with aliphatic hexaamine ligands are converted to new CH2Cl2 soluble tris(tetraarylborate)or 3BArf? salts (BArf = B(3,5-C6/s

Enantioselective Nitro-Michael Addition Catalyzed by N-Terminal Guanidinylated Helical Peptide

Enantioselective Michael addition of β-dicarbonyl compounds toward nitroalkenes were realized by using an immobilized, N-terminal-guanidinylated peptide, H2N?C(=NH)?Trp?Trp?(Leu?Leu?Aib)3?PEG?PS-resin (Aib=2-aminoisobutyric acid), as

Asymmetric 1,4-Addition Reactions Catalyzed by N-Terminal Thiourea-Modified Helical l-Leu Peptide with Cyclic Amino Acids

N-terminal thiourea-modified l-Leu-based peptide {(3,5-diCF3Ph)NHC(=S)-(l-Leu-l-Leu-Ac5c)2-OMe} with five-membered ring α,α-disubstituted α-amino acids (Ac5c) catalyzed a highly enantioselective 1,4-addition reaction between β-nitrostyrene and dimethyl malonate. The enantioselective reaction required only 0.5 mol % chiral peptide-catalyst in the presence of iPr2EtN (2.5 equiv.), and gave a 1,4-adduct with 93 % ee of an 85 % yield. As Michael acceptors, various β-nitrostyrene derivatives such as methyl, p-fluoro, p-bromo, and p-methoxy substituents on the phenyl group, 2-furyl, 2-thiophenyl, and naphthyl β-nitroethylenes could be applied. Furthermore, various alkyl malonates and cyclic β-keto-esters could be used as Michael donors. It became clear that the length of the peptide chain, a right-handed helical structure, amide N?Hs, and the N-terminal thiourea moiety play crucial roles in asymmetric induction.

Chiral Cobalt(III) Tris(1,2-diamine) Catalysts That Incorporate Nitrogenous Base Containing Anions for the Bifunctional Activation of Nucleophiles and Electrophiles in Enantioselective Addition Reactions

The lipophilic diastereomeric cobalt complexes Λ or Δ-[Co((S,S)-dpen)3]3+2Cl-BArf-(Λ or Δ-(S,S)-2 3+2Cl-BArf-; dpen/BArf-= 1,2-dipheny

Solvent free enantioselective catalysis with chiral cobalt(iii) Werner complexes via ball milling

Enantioselective additions of malonate esters to nitroalkenes can be catalyzed by a variety of salts of chiral cobalt(iii) trications [Co(1,2-diamine)3]3+ in the presence of nitrogen donor bases in acetone. Catalysts that feature enantiopure 1,2-diphenyle

Machine-Assisted Preparation of a Chiral Diamine Ligand Library and In Silico Screening Using Ab Initio Structural Parameters for Heterogeneous Chiral Catalysts

A ligand library containing 31 chiral diamines was synthesized using a flow-based semiautomatic reductive amination system. These ligands were evaluated in a continuous-flow asymmetric 1,4-addition reaction with a heterogeneous Ni catalyst. Based on the experimental results of ab initio DFT calculations, a prediction model for enantioselectivities was successfully constructed. Furthermore, virtual screening of possible ligands was conducted to identify promising structures, which showed good enantioselectivities in experiments. (Figure presented.).

Rendering classical hydrophilic enantiopure Werner salts [M(en)3]: N + n X- lipophilic (M/ n = Cr/3, Co/3, Rh/3, Ir/3, Pt/4); New chiral hydrogen bond donor catalysts and enantioselectivities as a function of metal and charge

Known hydrophilic halide salts of the title compounds are converted to new lipophilic BArf- (B(3,5-C6H3(CF3)2)4-) salts. These are isolated as hydrates (Λ- or Δ-[M(en)