Financial support from the European Research Council (ERC AdG 247014), the Swedish Research Council, and the Berzelii Centre EXSELENT is gratefully acknowledged.
Scalable Synthesis of Oxazolones from Propargylic Alcohols through Multistep Palladium(II) Catalysis: β-Selective Oxidative Heck Coupling of Cyclic Sulfonyl Enamides and Aryl Boroxines†
Article first published online: 31 OCT 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 51, pages 13745–13750, December 16, 2013
How to Cite
Alamsetti, S. K., Persson, A. K. Å., Jiang, T. and Bäckvall, J.-E. (2013), Scalable Synthesis of Oxazolones from Propargylic Alcohols through Multistep Palladium(II) Catalysis: β-Selective Oxidative Heck Coupling of Cyclic Sulfonyl Enamides and Aryl Boroxines. Angew. Chem. Int. Ed., 52: 13745–13750. doi: 10.1002/anie.201307471
- Issue published online: 17 DEC 2013
- Article first published online: 31 OCT 2013
- Manuscript Received: 25 AUG 2013
- European Research Council. Grant Number: ERC AdG 247014
- Swedish Research Council
- Berzelii Centre EXSELENT
- oxidative Heck coupling;
A whale of a scale: The title oxidative Heck coupling proceeded with unusual β selectivity to generate a variety of branched substituted oxazolones (see scheme; Ts=p-toluenesulfonyl). The three-step synthesis from readily available starting materials with a simple palladium catalyst and inexpensive reagents could be carried out in a single reaction vessel or scaled up for the preparation of large amounts of these amino acid precursors.