115276-75-0

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 104-94-9 4-methoxy-aniline 
• 64805-08-9 ethyl glyoxylate hydrate 
• 90-04-0 2-methoxy-phenylamine 
• 50845-77-7 N-(4-methoxy)phenylglycine ethyl ester 
• 617-37-8 oxalic acid monoethyl ester 

Downstream Products

• 690224-49-8 (S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

One-step synthesis of ethyl quinaldates by lewis acid catalyzed three-component coupling reaction of aromatic amines, aliphatic aldehydes and ethyl glyoxylate

A convenient, efficient and simple one-pot method for the synthesis of quinaldates was developed by three-component coupling reaction of an arylamine (1), ethyl glyoxylate and an aliphatic aldehyde (2) in the presence of Lewis acid catalyst. The reaction

Regio- and stereo-selective aza-Diels-Alder reaction of ethyl glyoxylate 4-methoxyphenylimine with 1,3-dienes in the presence of?BF3·Et2O. Evidence for a non-concerted mechanism

Cycloadditions of the glyoxylate imine 1 with 1-substituted and 1,4-disubstituted 1,3-dienes furnished tetrahydroquinoline compounds 4 and 5/15 with total regio- and stereo-control, except for one case where a mixture of isomers was formed. A stepwise mec

Catalysis of highly stereoselective Mannich-type reactions of ketones with ?±-imino esters by a pyrrolidine-sulfonamide. Synthesis of unnatural α-amino acids

The novel pyrrolidine-sulfonamide I has been prepared and used successfully to catalyze Mannich-type reactions between ketones and α-imino esters. The process is used to efficiently synthesize functionalized α-amino acid derivatives with excellent levels

Studies on the interaction of isocyanides with imines: Reaction scope and mechanistic variations

The interaction of imines with isocyanides has been studied. The main product results from a sequential process involving the attack of two units of isocyanide, under Lewis acid catalysis, upon the carbon-nitrogen double bond of the imine to form the 4-me

Chiral bifunctional organocatalysts in asymmetric aza-Morita-Baylis-Hillman reactions of ethyl (arylimino)acetates with methyl vinyl ketone and ethyl vinyl ketone

(Chemical Equation Presented) The bifunctional chiral phosphine Lewis base (R)-2′-diphenylphosphino-[1,1′-binaphthalene]-2-ol is an effective organocatalyst in the asymmetric aza-MBH reaction of ethyl (arylimino)acetates 1 with MVK and EVK to give the cor

Mechanochemical aza-vinylogous povarov reactions for the synthesis of highly functionalized 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-1,5-naphthyridines

The aza-vinylogous Povarov reaction between aromatic amines, α-ketoaldehydes or α-formylesters and α,β-unsaturated dimethylhydrazones was carried out in a sequential threecomponent fashion under mechanochemical conditions. Following extensive optimization

Asymmetric synthesis of piperidines using the nitro-Mannich reaction☆

A method for the synthesis of functionalized piperidines containing 3 contiguous stereocentres in the 2-,3- and 4- positions uses a diastereoselective nitro-Mannich to control stereochemistry. The nitro-Mannich reaction between a β-aryl/heteroaryl substituted nitroalkanes and glyoxylate imine provides β-nitro-amines with good selectivity (70:30 to >95:5) for the syn, anti-diastereoisomers. Reductive cyclisation with BF3.OEt2 and Et3SiH gave, after purification, stereochemically pure piperidines in 19–57% yield for ten examples with different 4-aryl/heteroaryl substituents.

Derivatives and application to the asymmetric synthesis of unnatural α-amino acid derivative

We describe herein a manganese(IV) oxide-mediated oxidation of N-p-methoxyphenyl (PMP)-protected glycine derivatives for the synthesis of a-imino carboxylic acid derivatives. Using this methodology, utilization of unstable glyoxic acid derivatives was avoided. Furthermore, using this methodology we synthesized novel a-imino carboxylic acid derivatives such as a-imino phenyl ester, perfluoroalkyl etsers, imides, and thioester. The asymmetric Mannich reaction of those novel imine derivatives with 1,3-dicarbonyl compound is also described, and the novel a-imino imide gave improved chemical yield and stereoselectivity compared with those obtained by the use of the conventional a-imino ester-type substrate.

A convenient method for preparation of α-imino carboxylic acid derivatives and application to the asymmetric synthesis of unnatural α-amino acid derivative

We describe herein a manganese(IV) oxide-mediated oxidation of N-p-methoxyphenyl (PMP)-protected glycine derivatives for the synthesis of α-imino carboxylic acid derivatives. Using this methodology, utilization of unstable glyoxic acid derivatives was avo

Copper-Catalyzed Addition of Alkylboranes to Iminoacetates: Access to α-Alkyl Branched α-Amino Acids

A copper(I)-catalyzed addition of alkylborane reagents to α-iminoacetates has been developed to assemble both acyclic and cyclic α-branched α-amino carboxylic acid derivatives in good yields. A wide variety of unactivated alkenes are well tolerated in this transformation. (Figure presented.).