We wish to thank Dr. Virginie Maggiotti for running NOE and decoupling experiments, Dr. Eli Ron and Dr. Phong Vu for useful discussions, and the NSF and the MDS Research Foundation for their financial support.
Regioselective Cyclizations Utilizing a Gold-Catalyzed [3,3] Propargyl Ester Rearrangement†
Article first published online: 15 AUG 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 37, pages 9398–9402, September 10, 2012
How to Cite
Cran, J. W. and Krafft, M. E. (2012), Regioselective Cyclizations Utilizing a Gold-Catalyzed [3,3] Propargyl Ester Rearrangement . Angew. Chem. Int. Ed., 51: 9398–9402. doi: 10.1002/anie.201203923
- Issue published online: 5 SEP 2012
- Article first published online: 15 AUG 2012
- Manuscript Revised: 21 JUN 2012
- Manuscript Received: 21 MAY 2012
- MDS Research Foundation
- synthetic methods
Switch-Au-roo: A new strategy for the regioselective synthesis of unsaturated carbocycles by chemoselective activation of a Rauhut–Currier zwitterion surrogate, formed from the Au-catalyzed [3,3] sigmatropic rearrangement of propargylic esters, has been achieved. By reversing the regiochemistry of the propargyl ester the synthesis of either the endo- or exocyclic enones is feasible.