106942-34-1

Upstream product

• 88058-32-6 2-benzoylamino-4-phenyl-butyric acid 
• 1012-05-1 D,L-homophenylalanine 
• 98-88-4 benzoyl chloride 
• 943-73-7 D-homophenylalanine 
• 150446-13-2 (S)-2-benzoylamino-4-phenylbutyric acid 

Downstream Products

• 106746-01-4 N-(3,3,3-Trifluoro-2-oxo-1-phenethyl-propyl)-benzamide 
• 106942-41-0 4-Phenethyl-2-phenyl-4-(2,2,2-trifluoro-acetyl)-4H-oxazol-5-one 
• 221071-30-3 C₂₀H₂₃NO₃ 

Relevant academic research and scientific papers

Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.

[8+2]formal cycloaddition reactions of tropones with azlactones under bronsted acid catalysis and synthesis of α-(2-tropyl), α-alkyl α-amino acids

The reaction of tropones with azlactones catalyzed by Bronsted acids affords a variety of dihydro-2H-cyclohepta[b]furan derivatives, corresponding to a formal [8+2] cycloaddition process. They can easily be opened by nucleophiles to afford a new type of α,α-disubstituted α-amino acid (or peptide) containing seven-membered rings at the quaternary position. The reaction of tropones with azlactones catalyzed by Bronsted acids affords a variety of dihydro-2H-cyclohepta[b]furan derivatives, corresponding to a formal [8+2] cycloaddition process. They can be easily opened by nucleophiles to afford a new type of α,α-disubstituted α-amino acid (or peptide) containing seven-membered rings at the quaternary position. Copyright

Formal Cycloaddition Reactions of Tropones with Azlactones under Br?nsted Acid Catalysis and Synthesis of α-(2-Tropyl), α-Alkyl α-Amino Acids

The reaction of tropones with azlactones catalyzed by Br?nsted acids affords a variety of dihydro-2H-cyclohepta[b]furan derivatives, corresponding to a formal [8+2] cycloaddition process. They can easily be opened by nucleophiles to afford a new type of α,α-disubstituted α-amino acid (or peptide) containing seven-membered rings at the quaternary position.

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.

SYNTHESIS OF FLUORINATED α-AMINO KETONES PART I: α-BENZAMIDOALKYL MONO- DI- AND TRIFLUOROMETHYL KETONES

2-Phenyl-5(4H)-oxazolones, obtained from α-amino acids, are reacted with di- and trifluoro acetic anhydride by a modified Dakin-West procedure to yield in a one-pot reaction α-benzamidoalkyl-di- and trifluoromethyl ketones in good yields.The monofluoromethyl analogues were also prepared from α-amino acids, however the use of the highly toxic fluoroacetic anhydride was avoided.The key step is the halogen exchange reaction on the corresponding bromomethyl ketone.