150446-13-2

Upstream product

• 943-73-7 D-homophenylalanine 
• 98-88-4 benzoyl chloride 
• 6310-42-5 S-2-amino-4-carbonyl-4-phenylbutyric acid hydrochloride 
• 1469876-42-3 C₂₆H₃₀N₂O₃ 
• 1401914-78-0 (S)-N-(1-furan-2-yl-3-phenylpropyl)benzamide 
• 89999-42-8 (S)-2-methoxymethyl-1-(3-phenylpropylidenamino)pyrrolidine 

Downstream Products

• 106942-34-1 2-phenyl-4-phenylethyl-5(4H)-oxazolone 
• 5765-24-2 2-benzoylamino-3,4-dihydro-2H-naphthalen-1-one 

Relevant academic research and scientific papers

Peptide-catalyzed conversion of racemic oxazol-5(4 H)-ones into enantiomerically enriched α-amino acid derivatives

We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

Asymmetric synthesis of α-(heteroaryl)alkylamines and α-amino acids via nucleophilic 1,2-addition of lithiated heterocycles to aldehyde SAMP-hydrazones

The asymmetric synthesis of α-(heteroaryl)alkylamines was accomplished by employing a diastereoselective nucleophilic 1,2-addition of lithiated aromatic heterocycles to aldehyde SAMP-hydrazones, followed by BH 3·THF or SmI2 promoted removal of the chiral auxiliary. The CBz or benzoyl-protected amines were obtained in good yields (40%-78%) and excellent enantiomeric excesses (ee = 88%-99%). The methodology can be applied to the synthesis of highly enantioenriched α-amino acids (ee = 90%-99%). TUeBITAK.

Asymmetric synthesis of α- And β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl) imines

The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected α- and β-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, α-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. α,α- Disubstituted α-amino esters with high enantiomeric purity can also be prepared when α-imino esters are the starting substrates.

Asymmetric synthesis of nonproteinogenic amino acids with l-amino acid transaminase: synthesis of (2S)-2-amino-4-oxo-4-phenylbutyric and (3E,2S)-2-amino-4-phenylbutenoic acids

2,4-Dioxo-4-phenylbutyric acid and 2-oxo-4-phenylbut-3-enoic acid are converted to the corresponding (S)-2-amino acids by recombinant Escherichia coli whole cells over-expressing aromatic transaminase from Enterobacter sp. BK2K-1 (AroATEs) in high yields (68-78%) and high enantiomeric purity (>99%) using l-aspartic acid as an amino donor.