We thank the NSF (CHE-0848324) and the University of Arizona for financial support.
Efficient Synthesis of Thiopyrans Using a Sulfur-Enabled Anionic Cascade†
Article first published online: 10 JAN 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 8, pages 1938–1941, February 20, 2012
How to Cite
Li, F., Calabrese, D., Brichacek, M., Lin, I. and Njardarson, J. T. (2012), Efficient Synthesis of Thiopyrans Using a Sulfur-Enabled Anionic Cascade. Angew. Chem. Int. Ed., 51: 1938–1941. doi: 10.1002/anie.201108261
- Issue published online: 14 FEB 2012
- Article first published online: 10 JAN 2012
- Manuscript Received: 23 NOV 2011
- NSF. Grant Number: CHE-0848324
- University of Arizona
- sulfur heterocycles;
- synthetic methods
The fifth element: An efficient new synthetic method for accessing 3,6-dihydro-2H-thiopyrans 1 in one pot has been developed. This method employs an anionic cascade, which is triggered by the addition of a vinyl nucleophile to a carbonyl group followed by S to O thiophosphate migration and an intramolecular thiolate displacement. The scope is demonstrated for a range of ketone and ester substrates.