Development of a gold(I)-catalyzed aromatic Claisen rearrangement

ORGN 217

James R. Vyvyan, vyvyan@chem.wwu.edu, Jennifer K. Johnson, Laura D. Steffens, steffel@cc.wwu.edu, and Rebecca A. Swanson. Department of Chemistry, Western Washington University, 516 High Street, Bellingham, WA 98225-9150
Triphenylphosphinegold(I) triflate catalyzes the conversion of aryl allyl ethers to the corresponding [3,3]- (Claisen) and [1,3]-rearrangement products. The product distribution depends on the stereochemistry of the olefin in the allylic ether as well as the positions and electronic properties of the aryl substituents. Experiments to probe the scope, limitations, and mechanism of this reaction will be discussed.

 

Metal-Mediated Reactions and Synthesis
8:00 AM-12:00 PM, Monday, April 7, 2008 Morial Convention Center -- Rm. R06, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008