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Issue 48, 2015
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Continuous-flow thermolysis for the preparation of vinylglycine derivatives

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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.

Graphical abstract: Continuous-flow thermolysis for the preparation of vinylglycine derivatives

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Supplementary files

Article information


Submitted
30 Sep 2015
Accepted
03 Nov 2015
First published
03 Nov 2015

Org. Biomol. Chem., 2015,13, 11602-11606
Article type
Communication
Author version available

Continuous-flow thermolysis for the preparation of vinylglycine derivatives

N. Lamborelle, J. F. Simon, A. Luxen and J. M. Monbaliu, Org. Biomol. Chem., 2015, 13, 11602
DOI: 10.1039/C5OB02036K

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