title: Synthesis of (R)-alpha-benzylmethionine: a novel rearrangement during alkylation of the Seebach (R)-methionine oxazolidinone.
abstract: 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)-alpha-benzyl-methionine was obtained in 78% yield and in an enantiomeric ratio of 90:10.
authors.affiliation: GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, UK SG1 2NY. pan.a.procopiou@gsk.com
authors.forename: Panayiotis A
authors.initials: PA
authors.lastname: Procopiou
authors.forename: Mahmood
authors.initials: M
authors.lastname: Ahmed
authors.forename: Séverine
authors.initials: S
authors.lastname: Jeulin
authors.forename: Rossana
authors.initials: R
authors.lastname: Perciaccante