Colorado State University is acknowledged for the support of our program. Eli Lilly is gratefully acknowledged for a graduate research fellowship to D.A.R.
Stereoselective Synthesis of Tetrasubstituted Olefins through a Halogen-Induced 1,2-Silyl Migration†
Article first published online: 10 JUN 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 29, pages 7579–7582, July 15, 2013
How to Cite
Barczak, N. T., Rooke, D. A., Menard, Z. A. and Ferreira, E. M. (2013), Stereoselective Synthesis of Tetrasubstituted Olefins through a Halogen-Induced 1,2-Silyl Migration . Angew. Chem. Int. Ed., 52: 7579–7582. doi: 10.1002/anie.201303007
- Issue published online: 11 JUL 2013
- Article first published online: 10 JUN 2013
- Manuscript Received: 11 APR 2013
- Eli Lilly
- alkene geometry;
Migrating through Si valley: The highly stereoselective formation of α-silyl-β- haloenones by way of silicon group migration is described. Electrophilic activation of the alkyne by N-halosuccinimides induced an anti-selective migration to give highly substituted enones (see scheme). These enone products can be readily converted to the all-carbon tetrasubstituted alkenes while maintaining their geometry.