The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions
Tran, Duc N
Ingham, Richard J
Organic & Biomolecular Chemistry
Royal Society of Chemistry
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Glöckner, S., Tran, D. N., Ingham, R. J., Fenner, S., Wilson, Z., Battilocchio, C., & Ley, S. V. (2014). The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions. Organic & Biomolecular Chemistry, 13 207-214. https://doi.org/10.1039/C4OB02105C
A rapid flow synthesis of oxazolines and their oxidation to the corresponding oxazoles is reported. The oxazolines are prepared at room temperature in a stereospecific manner, with inversion of stereochemistry, from β-hydroxy amides using Deoxo-Fluor®. The corresponding oxazoles can then be obtained via a packed reactor containing commercial manganese dioxide.
We are grateful to the Swiss National Science Foundation (DNT), the Ralph Raphael fellowship (RJI), the German Academic Exchange Service DAAD (SF), the Royal Society Newton International Fellowship (ZEW), Pfizer Worldwide Research and Development (CB) and the EPSRC (SVL, SF and ZEW, grant nº EP/K0099494/1) for financial support. The Labtrix Start was kindly loaned by Chemtrix BV and the liquid-liquid phase separator by Zaiput Flow Technologies (we are grateful to Dr Andrea Adamo for technical support with this device).
External DOI: https://doi.org/10.1039/C4OB02105C
This record's URL: https://www.repository.cam.ac.uk/handle/1810/246399
Attribution-NonCommercial 2.0 UK: England & Wales
Licence URL: http://creativecommons.org/licenses/by-nc/2.0/uk/