Continuous-flow thermolysis for the preparation of vinylglycine derivatives
Nicolas Lamborelle1, Justine F Simon, André Luxen
1Center for Integrated Technology and Organic Synthesis, Department of Chemistry, University of Liège, 4000 Liège, Belgium. jc.monbaliu@ulg.ac.be.
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.
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