Continuous-flow thermolysis for the preparation of vinylglycine derivatives

[en] 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.

Disciplines :

Chemistry

Author, co-author :

Lamborelle, Nicolas ; Université de Liège > Département de chimie (sciences) > Département de chimie (sciences)

Simon, Justine ; Université de Liège > Centre de recherches du cyclotron

Luxen, André ; Université de Liège > Département de chimie (sciences) > Laboratoire de chimie organique de synthèse

Monbaliu, Jean-Christophe ; Université de Liège > Département de chimie (sciences) > Center for Integrated Technology and Organic Synthesis

Language :

English

Title :

Continuous-flow thermolysis for the preparation of vinylglycine derivatives

Publication date :

2015

Journal title :

Organic and Biomolecular Chemistry

ISSN :

1477-0520

eISSN :

1477-0539

Publisher :

Royal Society of Chemistry, Cambridge, United Kingdom

Volume :

Pages :

11602-11606

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 30 November 2015

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