An improved protocol for the preparation of (S)-vinylglycine from (S)-methionine.
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.
Küchenthal
Christian-H
CH
Institute of Organic Chemistry, Justus Liebig University Giessen, Heinrich-Buff-Ring 58, 35392, Giessen, Germany.
Migenda
Julia
J
Polednia
Magdalena
M
Maison
Wolfgang
W
D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008715:Methionine / Q000737:chemistry*; D013237:Stereoisomerism
C006507:vinylglycine; D008715:Methionine; D005998:Glycine