61924-67-2

Upstream product

• 55895-90-4 (±)-ethyl 2-amino-3-(4-methoxyphenyl)propanoate 
• 123-11-5 4-methoxy-benzaldehyde 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 35388-38-6 2-(4-methoxyphenyl)-1-nitro-1-ethoxycarbonylethene 
• 219554-67-3 ethyl 2-bromo-3-(4-methoxyphenyl)propionate 

Downstream Products

• 949511-15-3 ethyl 3-(4-methoxyphenyl)-2-methyl-2-nitropropionate 
• 55895-90-4 (±)-ethyl 2-amino-3-(4-methoxyphenyl)propanoate 
• 25441-65-0 2-amino-3-(4-methoxyphenyl)-2-methylpropionic acid ethyl ester 

Relevant academic research and scientific papers

Enantioselective Addition of α-Nitroesters to Alkynes

By using Rh–H catalysis, we couple α-nitroesters and alkynes to prepare α-amino-acid precursors. This atom-economical strategy generates two contiguous stereocenters, with high enantio- and diastereocontrol. In this transformation, the alkyne undergoes isomerization to generate a RhIII–π-allyl electrophile, which is trapped by an α-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic α-nitroesters to the corresponding α,α-disubstituted α-amino esters.

Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions

We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.

IMIDAZOPYRAZINE DERIVATIVES, PROCESS FOR PREPARATION THEREOF, AND THEIR USES AS LUCIFERINS

The present invention is in the field of bioluminescence in biology and/or medicine. In particular, the invention provides imidazopyrazine derivatives, processes for preparation thereof, and their uses as luciferins.

Transforming natural amino acids into α-alkyl-substituted amino acids with the help of the HOF·CH3CN complex

(Chemical Equation Presented) α-Alkyl amino acids can be efficiently prepared in high yields from the respective amino acids themselves. The key step is the oxidation of the amine function to create the corresponding α-nitro acid in a fast and very high yield reaction followed by phase-transfer alkylation and finally reduction to the desired α-alkyl amino acid. Several such acids containing aromatic rings or additional carboxylic groups and acids with steric hindrance at the α-position are suitable substrates. Several alkyl halides were examined as alkylating agents.