42798-15-2

Upstream product

• 4553-07-5 ethyl phenylcyanoacetate 
• 83-13-6 diethyl 2-phenylmalonate 
• 113932-23-3 2-chlorocarbonyl-2-phenyl-acetic acid ethyl ester 
• 17097-90-4 2-phenylmalonic acid monoethyl ester 

Downstream Products

• 51431-13-1 phenylmalonamic acid 
• 1190830-44-4 (R)-di-tert-butyl 1-(1-amino-3-ethoxy-1,3-dioxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate 
• 874016-52-1 2,2-dimethyl-4-oxo-5-phenyl-oxazolidine-5-carboxylic acid menthyl ester 
• 874016-51-0 (-)-2-hydroxy-2-phenyl-malonamic acid menthyl ester 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 7505-92-2 2-oxo-2-phenylacetamide 
• 874016-48-5 2-phenyl-malonamic acid menthyl ester 
• 1303612-82-9 3-amino-1-ethoxy-2-hydroxy-2-phenyl-1,3-dioxopropane 

Relevant academic research and scientific papers

Managing highly coordinative substrates in asymmetric catalysis: A catalytic asymmetric amination with a lanthanum-based ternary catalyst

Full details of a catalytic asymmetric amination with a lanthanum/amide-based ligand catalyst system are described. A catalyst comprising La(NO3)3·6H2O, (R)-3a and H-D-Val-OtBu was identified to promote the catalytic asymmetric amination of nonprotected succinimide derivative 1 with as little as 1 mol % catalyst loading. Mechanistic studies by various spectroscopic analyses and several control and kinetic experiments suggested that the catalyst components were in equilibrium between the associated and dissociated forms, and that the reaction likely proceeded through a La(NO3)3· 6H2O/(R)-3a/H-D-Val-OtBu ternary complex. This catalyst system was also effective for asymmetric amination of N-nonsubstituted α-alkoxycarbonyl amides 7, hitherto unprecedented substrates in asymmetric catalysis, probably due to their attenuated reactivity and difficult stereocontrol, affording the amination products in up to >99% yield and >99% ee. The high catalytic performance and enantiocontrol of the reaction with highly coordinative substrates were achieved by the activation/recognition of the substrates exerted by coordination to lanthanum and hydrogen bonding cooperatively in the transition state.

Oxidation of chiral α-phenylacetate derivatives: Formation of dimers with contiguous quaternary stereocenters versus tertiary alcohols

The menthol esters of α-phenylacetate derivatives undergo diastereoselective oxidative dimerizations (α-cyano) in the presence of oxidants, and nitrosylation (α-amido) in the presence of CAN to form products containing adjacent functionalized quaternary stereocenters and tertiary alcohols, respectively.

Malonamic acid derivatives as M1 selective muscarinic receptor antagonists

A series of malonamic acid esters with suitable amino alcohols, typical of antimuscarinic compounds, was synthesized and the affinities for the three pharmacologically defined muscarinic receptor subtypes, namely M1, M2 and M3/