We acknowledge generous funding from ACS-PRF (50491-DNI) and the University of Illinois at Chicago. We also thank Prof. T. Driver and group for insightful discussions.
Preparation of α-Oxygenated Ketones by the Dioxygenation of Alkenyl Boronic Acids†
Article first published online: 28 JUN 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 31, pages 7799–7803, July 27, 2012
How to Cite
Patil, A. S., Mo, D.-L., Wang, H.-Y., Mueller, D. S. and Anderson, L. L. (2012), Preparation of α-Oxygenated Ketones by the Dioxygenation of Alkenyl Boronic Acids . Angew. Chem. Int. Ed., 51: 7799–7803. doi: 10.1002/anie.201202704
- Issue published online: 25 JUL 2012
- Article first published online: 28 JUN 2012
- Manuscript Received: 7 APR 2012
- ACS-PRF. Grant Number: 50491-DNI
- University of Illinois at Chicago
- boronic acids;
Two in two: Dioxygenation of alkenyl boronic acids has been achieved with N-hydroxyphthalimide. The two-step process involves etherification of an alkenyl boronic acid with N-hydroxyphthalimide followed by a [3,3] rearrangement. The dioxygenated product can then be hydrolyzed to form either the corresponding α-hydroxy ketone or the α-benzoyloxy ketone.