Synthesis of α-substituted α-amino acids by the alkylation of 5-oxazolinone derivatives

Abstract

Methods have been developed for the alkylation of 5-oxazolinone derivatives in DMF in the presence of K₂CO₃, KOH, or diisopropylethylamine and a phase transfer catalyst as well as for the preparation of α-methylphenylalanine, α-methylalanine, α-methylalanine, and the methyl ester of N-benzoyl-α-methylalanine. Increasing the initial concentration of the starting 5-oxazolinone in the reaction mixture leads to a sharp drop in the yield of reaction products due to side condensation reactions. The reaction of 2-phenyl-4-benzyl-5- oxazolinone with ethyl iodide gave a dimer namely, 3-(benzoylamino)-3,5-dibenzylpyrrolidine-2,4-dione.

How to Cite
Slavinskaya, V. A.; Sile, D. É.; Katkevich, M. Yu.; Korchagova, É. Kh.; Lukevits, É. Chem. Heterocycl. Compd. 1994, 30, 724. [Khim. Geterotsikl. Soedin. 1994, 829.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01166316