773148-47-3

Upstream product

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

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

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.).

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

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)