title: An improved protocol for the preparation of (S)-vinylglycine from (S)-methionine.
abstract: We present an optimized procedure for the synthesis of (S)-vinylglycine from (S)-methionine. The key step is a solvent free pyrolysis of an intermediate sulfoxide at high temperature. Using our optimized reaction conditions, Cbz-protected vinylglycine was obtained in high yield and with almost no side products. The protocol is scalable, fast and avoids the use of poisonous reagents.
authors.affiliation: Institute of Organic Chemistry, Justus Liebig University Giessen, Heinrich-Buff-Ring 58, 35392, Giessen, Germany.
authors.forename: Christian-H
authors.initials: CH
authors.lastname: Küchenthal
authors.forename: Julia
authors.initials: J
authors.lastname: Migenda
authors.forename: Magdalena
authors.initials: M
authors.lastname: Polednia
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Maison
mesh_terms: D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008715:Methionine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C006507:vinylglycine; D008715:Methionine; D005998:Glycine