The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions.
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Authors
Abstract
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.
Description
Keywords
Amides, Chemistry Techniques, Synthetic, Kinetics, Manganese Compounds, Oxazoles, Oxidation-Reduction, Oxides
Journal Title
Org Biomol Chem
Conference Name
Journal ISSN
1477-0520
1477-0539
1477-0539
Volume Title
13
Publisher
Royal Society of Chemistry (RSC)
Publisher DOI
Sponsorship
Engineering and Physical Sciences Research Council (EP/K009494/1)
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).