138604-90-7

Upstream product

• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 786589-52-4 [(E)-Methoxycarbonylimino]-acetic acid methyl ester 
• 121-69-7 N,N-dimethyl-aniline 
• 444997-85-7 (4-aminophenyl)methoxycarbonylaminoacetic acid methyl ester 
• 100508-82-5 2-(Methoxycarbonylimino)-2-phenylessigsaeure-methylester 
• 444997-80-2 (R)-(4-dimethylaminophenyl)methoxycarbonylaminoacetic acid methyl ester 

Relevant academic research and scientific papers

NADH model mediated reduction of C=N substrates: Enantioselective synthesis of D- and L-phenylglycinates

Hydride transfer from N,N,1,2,4-pentamethyl-1,4-dihydronicotinamide, 1, to methyl 2-methoxycarbonylimino-phenylacetate, 3, was accomplished in an optical yield ≥95%.

Optically active aromatic and heteroaromatic α-amino acids by a one-pot catalytic enantioselective addition of aromatic and heteroaromatic C-H bonds to α-imino esters

The development of a practical one-pot catalytic enantioselective procedure for the synthesis of non-natural aromatic and heteroaromatic α-amino acids is reported. Starting from readily available starting materials and application of a chiral BINAP-Cu(I) catalyst, the optically active products are formed with readily removable N-protecting groups. The scope of the reaction is demonstrated by the addition of substituted furans, thiophenes, pyrroles, and aromatic compounds to N-alkoxy-carbonyl-α-imino esters in good yields and with enantioselectivities up to 96% ee for the furans, 93% ee for the thiophenes, and 98% for the aromatic compounds. The protecting groups are readily removed, and various transformations of the aromatic and heteroaromatic a-amino acids are demonstrated. The coordination of the N-alkoxycarbonyl α-imino ester to the chiral BINAP-Cu(I) complex and the enantioselectivity of the catalyst is discussed on the basis of the DFT calculations and X-ray crystallographic data.

Enantioselective reduction of C=O and C=N compounds with NADH model N,N,1,2,4-pentamethyl-1,4-dihydronicotinamide

The scope and mechanism of enantioselective hydride transfer from NADH model 4 to prochiral C=O and C=N compounds were investigated. Efficient chirality transfer from 4 to α-keto esters and α-methoxycarbonylimino esters was achieved. The resemblance in reactivity and stereochemistry of the prochiral C=O and C=N-CO2Me functionalities in the hydride transfer reaction is attributed to the intervention of a similar Mg(ClO4)2-mediated ternary complex.