75445-32-8

Upstream product

• 100-52-7 benzaldehyde 
• 105-34-0 methyl 2-cyanoacetate 
• 39687-95-1 isocyanoacetic acid methyl ester 

Downstream Products

• 75445-33-9 trans-4-Hydroxymethyl-5-phenyl-2-oxazolin 
• 120134-07-8 cis-4-(methoxycarbonyl)-4-isopropyl-2,5-diphenyl-2-oxazoline 
• 120134-06-7 methyl 2-amino-2-isopropyl-3-phenyl-3-benzoyloxypropionate 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 19185-47-8 trans-2,5-diphenyl-4-methoxycarbonyl-4,5-dihydrooxazole 

Relevant academic research and scientific papers

New Insights into Aldol Reactions of Methyl Isocyanoacetate Catalyzed by Heterogenized Homogeneous Catalysts

The Hayashi-Ito aldol reaction of methyl isocyanoacetate (MI) and benzaldehydes, a classic homogeneous Au(I)-catalyzed reaction, was studied with heterogenized homogeneous catalysts. Among dendrimer encapsulated nanoparticles (NPs) of Au, Pd, Rh, or Pt lo

Highly active copper-network catalyst for the direct aldol reaction

The development of a highly active solid-phase catechol-copper network catalyst for direct aldol reaction is described. The catalyst was prepared from an alkyl-chain-linked bis(catechol) and a copper(II) complex. The direct aldol reaction between carbonyl

Highly diastereo- and enantioselective aldol reaction of methyl α-isocyanoacetate: A cooperative catalysis approach

The cooperative catalyst activity between a chiral transition-metal catalyst and an achiral organocatalyst has been identified as one of the critical asymmetric reaction optimization components in the highly diastereo- and enantioselective aldol reaction

Catalytic performance of symmetrical and unsymmetrical sulfur-containing pincer complexes: Synthesis and tandem catalytic activity of the first PCS-pincer palladium complex

The synthesis and catalytic applications of a new aryl-based unsymmetrical PCS-pincer complex are reported. Preparation of the robust air- and moisture-stable PCS-pincer palladium complex 5[X] started from the symmetrical α,α′-dibromo-meta-xylene and involved the selective substitution of one bromide by PPh2(BH3), followed by substitution of the second bromide by SPh and subsequent introduction of the palladium. The new PCS complexes (5[X]) were employed as catalysts in two important organic transformations. Firstly, complex 5[Cl] displays high catalytic activity in aldol reactions but enters the catalytic cycle as a precatalyst. Secondly, complex 5- [BF4] displays tandem catalytic activity in the coupling of allyl chlorides with aldehydes and imines in the presence of hexamethylditin. In these tandem catalytic reactions the first process is the conversion of allyl chlorides into trimethylallyltin (and trimethyltin chloride) with Sn2Me6, which is followed by catalytic allylation of aldehyde and sulfonimine substrates. In addition, we present a new catalytic process for the one-pot allylation of 4-nitrobenzalde-hyde with vinyloxirane. The catalytic performance of the novel PCS-pincer palladium complex was compared to those of its symmetrical PCP- and SCS-pincer complex analogues. It was concluded that the unsymmetrical PCS complex advantageously unifies the attractive catalytic features of the corresponding symmetrical pincer complexes including both (π-) electron-withdrawing (such as phosphorus) or (σ-) electron-donating (such as sulfur and nitrogen) heteroatoms. Thus, in the aldol reaction the PCS-pincer palladium complex 5[X] provides a high turnover frequency, while in the tandem process both reactions are catalysed with sufficiently high activity.

Diastereopure cationic NCN-pincer palladium complexes with square planar η4-N,C,N,O coordination

Neutral NCN-pincer palladium bromide complex 2 containing the monoanionic, enantiopure pincer ligand 2,6-bis{[(S)-2-hydroxymethyl-1-pyrrolidinyl]methyl} phenyl bromide (1) with bis-ortho-(S)-prolinol substituents was synthesized and isolated as a mixture

Ionic core-shell dendrimers with an octacationic core as noncovalent supports for homogeneous catalysts

Ionic core-shell dendrimers with an octacationic core have been applied as noncovalent supports for homogeneous catalysts. Catalytically active arylpalladium complexes, which bear a tethered sulfato group, were noncovalently attached to the ionic core-she

Copper(I)-catalyzed diastereoselective formation of oxazolines and N-sulfonyl-2-imidazolines

A simple and short method for the reaction of methyl isocyanoacetate with aldehydes and N-sulfonylimines is presented. The reaction is catalyzed by copper(I) complexes and proceeds with excellent yields and high diastereoselectivities.

Pyrenoxy-based NCN-pincer palladium(II) molecular tweezers: Synthesis, properties in solution and catalysis

A highly flexible molecular tweezer, (aqua) (2,6-bis[(dimethylamino)methyl]-4-{3-[(1-pyrenyloxy)methyl]-5- (trimethylsilyl)benzyloxy}phenyl)palladium(II) tetrafluoroborate (1a), constructed from a para-hydroxy-functionalized NCN-pincer palladium(II) complex {NCN-OH = [2,6-(Me2NCH2)2 C6H2-4-OH]}, a pyrenoxy unit and a xylyl spacer, was synthesized. X-ray analysis of the structure of 1-[3-({3,5-bis[(dimethylamino)methyl]-4-(trimethylsilyl) phenyloxy}methyl)-5-bromobenzyloxy]pyrene (10), a precursor ligand of la, showed a completely flattened conformation in the solid state, imposed by favorable intramolecular π-stacking interactions. The molecular structure of la in solution proved to be fluxional on the NMR timescale. UV/Vis and (time-resolved) fluorescence spectroscopy revealed that, in spite of the high flexibility, the catalyst and pyrenoxy units are in close proximity because of cation-π interactions. This was further supported by conformer searches using molecular mechanics (MM2). The binding affinity of picric acid towards the pyrenoxy moiety was studied by 1H NMR titrations, revealing association constants Ka in the order of 101 to 102 M-1. Tweezer la shows small rate enhancements in aldol condensations of aromatic aldehydes with methyl isocyanoacetate compared to (aqua)(2,6-bis[(dimethylamino)methyl]4-{[3-(trimethylsilyl) benzyloxy}phenyl)palladium(II) tetrafluoroborate (2), which lacks the pyrenoxy unit. The tweezer was immobilized on a G2-carbosilane dendrimer, generating the dendritic (aqua)(G2-carbosilane)palladium complex 1b, showing a decreased catalytic activity compared to 1a. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

A polycationic dendrimer as noncovalent support for anionic organometallic complexes

Polycationic dendrimer 1 forms a well-defined, stoichiometric assembly with eight anionic metal complexes; this assembly is successfully applied as a Lewis acidic catalyst which performs comparably to the unsupported metal complex.

New mono- and tricyclopalladated dendritic systems with encapsulated catalytic sites

The preparation of a series of new macrocyclic carbodiazasilane molecules functionalized with the monoanionic [2,6-(CH2NMe2)2C6H3] - ≡ N,C,N-pincer ligand has been accomplished. Palladation