title: Continuous-flow thermolysis for the preparation of vinylglycine derivatives.
abstract: Syn sulfoxide elimination was carried out under continuous-flow conditions in a mesofluidic thermolysis reactor. The design of the reactor enabled accurate control of reaction time and conditions, affording a convenient scale-independent procedure for the production of N,C-protected vinylglycine derivatives. Thermolysis at 270 °C under 1000 psi of pressure in superheated toluene enabled typical daily outputs ranging from 11 to 46 g per day with excellent selectivities and ee (>97%). The various competitive reaction pathways were studied and rationalized according to a computational study.
authors.affiliation: Center for Integrated Technology and Organic Synthesis, Department of Chemistry, University of Liège, 4000 Liège, Belgium. jc.monbaliu@ulg.ac.be.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Lamborelle
authors.forename: Justine F
authors.initials: JF
authors.lastname: Simon
authors.forename: André
authors.initials: A
authors.lastname: Luxen
authors.forename: Jean-Christophe M
authors.initials: JC
authors.lastname: Monbaliu
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006358:Hot Temperature; D008715:Methionine / Q000031:analogs & derivatives / Q000737:chemistry; D014050:Toluene / Q000737:chemistry
chemical_list: D014050:Toluene; C006507:vinylglycine; D008715:Methionine; D005998:Glycine; C013111:methionine sulfoxide