188488-62-2

Upstream product

• 51335-08-1 (4-methoxy-phenylimino)-phenyl-acetic acid methyl ester 
• 1179348-58-3 methyl 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-2-phenylacetate 
• 104-94-9 4-methoxy-aniline 
• 125990-08-1 methyl α-(p-methoxyphenylamino)-α-phenylacetate 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 22979-35-7 Methyl phenyldiazoacetate 
• 67-56-1 methanol 

Downstream Products

• 6591-61-3 (S)-Phenylglycine methyl ester 

Relevant academic research and scientific papers

Organocatalytic asymmetric synthesis of α-amino esters from sulfoxonium ylides

Described here is the first organocatalytic asymmetric N-H insertion reaction of α-carbonyl sulfoxonium ylides. Without a metal catalyst, this reaction represents an attractive complement to the well-established carbene insertion reactions. As a stable surrogate of diazocarbonyl compounds, sulfoxonium ylides reacted with a range of aryl amines to provide efficient access to α-aryl glycines with excellent enantiocontrol in the presence of a suitable chiral phosphoric acid catalyst. The high stability and weak basicity of sulfoxonium ylides not only enable this protocol to be user-friendly and practically useful, but also preclude catalyst decomposition, which is crucial to the excellent amenability to electron-poor amine nucleophiles. Detailed mechanistic studies indicated that the initial protonation is reversible and the C-N bond formation is rate-determining.

Dynamic kinetic resolution of α-chloro esters in asymmetric nucleophilic substitution using diacetone-D-glucose as a chiral auxiliary

Diacetone-D-glucose mediated dynamic kinetic resolution of α-chloro-α-aryl esters in nucleophilic substitution reactions has been investigated. Reactions of various amine nucleophiles in the presence of TBAI and DIEA can provide the substitution products 2-10 up to 97% yield and 97:3 dr. This simple procedure with easy removal of the chiral auxiliary provides a practical protocol for asymmetric syntheses of α-amino acid derivatives up to 97:3 er.

Rh-catalyzed asymmetric hydrogenation of α-aryl imino esters: An efficient enantioselective synthesis of aryl glycine derivatives

(Chemical Equation Presented) A highly enantioselective synthesis of aryl glycine derivatives from asymmetric hydrogenation was achieved by subjecting N-PMP-protected α-aryl imino esters to hydrogenation under Rh-bisphosphine catalysis (see scheme; PMP = para-methoxyphenyl, cod = cycloocta-1,5-diene). The PMP group could be easily removed for the preparation of enantiomerically pure aryl glycine derivatives.

Cooperative copper-squaramide catalysis for the enantioselective N-H insertion reaction with sulfoxonium ylides

The first examples of a highly efficient and enantioselective carbene-mediated insertion reaction, from a sulfur ylide, are described. By way of a catalytic asymmetric insertion reaction into N-H bonds from carbonyl sulfoxonium ylides and anilines, using a copper-bifunctional squaramide cooperative catalysis approach, thirty-seven α-arylglycine esters were synthesized in enantiomeric ratios up to 92?:?8 (99?:?1 after a single recrystallization) and reaction yields ranging between 49-96%. Furthermore, the protocol benefits from quick reaction times and is conducted in a straightforward manner.

Nitrogen-Doped Carbon Enables Heterogeneous Asymmetric Insertion of Carbenoids into Amines Catalyzed by Rhodium Nanoparticles

Development of stable heterogeneous catalyst systems is a crucial subject to achieve sustainable society. Though metal nanoparticles are robust species, the study of asymmetric catalysis by them has been restricted because methods to activate metal nanopa

Synthesis method of chiral alpha-amino acid ester derivative

The invention discloses a synthesis method of a chiral alpha-amino acid ester derivative. The chiral alpha-amino acid ester derivative is prepared by catalyzing asymmetric hydrogenation of imino acidester by taking a complex prepared in situ through react

Chiral bipyridine-annulated bicyclo[3.3.1]nonane N-oxide organocatalysts for stereoselective allylation and hydrosilylation reactions

The synthesis of chiral C2-symmetric bis(bipyridine N,N′-dioxide) and bis(bipyridine N-monooxide) derivatives featuring bipyridine-annulated bicyclo[3.3.1]nonane framework is reported. The new Lewis basic bipyridine N,N′-dioxides exhibited good

Aerobic redox deracemization of α-aryl glycine esters

An effective redox deracemization of α-aryl glycine esters has been described. The one-pot redox process consisted of copper(II) catalysis using molecular oxygen as terminal oxidant and chiral phosphoric acid catalyzed asymmetric transfer hydrogenation wi

Ir-catalyzed Asymmetric Hydrogenation of α-Imino Esters with Chiral Ferrocenylphosphine-Phosphoramidite Ligands

An Ir-catalyzed asymmetric hydrogenation of α-imino esters with unsymmetrical hybrid chiral ferrocenylphosphine-phosphoramidite ligands for the synthesis of optically active α-aryl glycines has been described. The result indicated that the presence of the iodo-substitutent at the 3/3’-position of the binaphthyl unit of ligand could significantly improve the catalytic performance. This method features high asymmetric induction and reasonable functional group tolerance, thus providing a concise and efficient approach toward chiral α-aryl glycine derivatives with up to 96% ee.

Chiral 1,8-naphthyridine based ligands: Syntheses and characterization of Di- and tetranuclear copper (I) and silver (I) complexes

Oxazoline and camphor-pyrazole units are introduced on the 1,8-naphthyridine scaffold to access chiral ligands L1, L2 and L3. Metalation of these chiral ligands with Cu(I) and Ag(I) precursors afforded di- and tetranuclear complexes [Cu4I4(L1)2] (1), [Cu4I4(L2)2] (2), [Cu2I2(L3)] (3), [Cu2I(L2)2](OTf) (4), [Ag2(L1)2](OTf)2 (5) and [Ag4(L2)4Br](OTf)3 (6), containing [M4Xn] (n = 1,4 and X = Br, I) or [M2Xn] (n = 0, 1, 2 and X = I) core. All complexes are structurally characterized. Naphthyridine-derived ligands reveal bridge-chelate coordination motif and hold two metal centers in close proximity. The tetranuclear complexes are dimer of dinuclear complexes bridged by the halides. Electronic absorption and emission spectra of copper complexes are reported. Catalytic utility of all complexes are examined for asymmetric transformations but they showed poor activity probably due to limited solubility and coordinative saturation at the metal centers. The best results are obtained with [L3/Cu salt] combination for cyclopropanation of styrene, N–H bond insertion and nitroaldol (Henry) reactions with very low enantioselectivity.