100508-79-0

Upstream product

• 171181-53-6 methyl N^α-(diphenylmethylene)-DL-phenylglycinate 
• 79-03-8 propionyl chloride 
• 24461-61-8 phenylglycine methyl ester 
• 15028-40-7 DL-2-phenylglycine methyl ester hydrochloride 

Downstream Products

• 97485-14-8 2-Ethyl-4-phenyl-4H-oxazol-5-one 
• 15962-45-5 N-Propionyl-DL-phenylglycin 
• 100508-86-9 2-(Propionylamino)-2-hydroxy-2-phenylessigsaeure-methylester 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 100508-81-4 2-(Propionylimino)-2-phenylessigsaeure-methylester 

Relevant academic research and scientific papers

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

N-Acyl-α-imino Acid Derivatives, II. - Synthesis of N-Acylimines of Methyl Phenylglyoxylate

The title compounds 8 are obtainable via treatment of phenylglycine methyl ester (2) with tert-butyl hypochlorite or by direct dehydrogenation of the N-acylphenylglycine ester 6 with N-bromosuccinimide.