649723-56-8Relevant academic research and scientific papers
Synthesis of (R)-α-benzylmethionine: a novel rearrangement during alkylation of the Seebach (R)-methionine oxazolidinone
Procopiou, Panayiotis A.,Ahmed, Mahmood,Jeulin, Severine,Perciaccante, Rossana
, p. 2853 - 2858 (2003)
Alkylation of the enolate of the Seebach (R)-methionine oxazolidinone with benzyl bromide gave the expected benzylated product in low yield. The major product was a novel amine arising from oxazolidinone cleavage, decarboxylation, alkylation and finally hydrolysis. The rearrangement could be suppressed by using a more reactive electrophile or by using the N-Cbz instead of the N-benzoyl protecting group, and the required (R)-α-benzyl-methionine was obtained in 78% yield and in an enantiomeric ratio of 90 : 10.
