Gold(I)-catalyzed aromatic Claisen rearrangement: Effects of allyl ether structure on product distribution

ORGN 158

James R. Vyvyan, vyvyan@chem.wwu.edu, Laura D. Steffens, steffel@cc.wwu.edu, Rebecca A. Swanson, and Jennifer K. Johnson. Department of Chemistry, Western Washington University, 516 High Street, Bellingham, WA 98225-9150
The aromatic Claisen rearrangement is a powerful tool for the formation of new C-C bonds from aryl allyl ethers. We have found that gold(I) phosphine complexes catalyze the conversion of aryl allyl ethers to the corresponding [3,3]- (Claisen) and [1,3]-rearrangement products. The product distribution changes depending on the stereochemistry of the allylic ether substrate and the position of the aryl substituents. The E-allyl ether produces mostly [1,3]-rearrangement product while the Z-allyl ether produces mostly Claisen product. Current results and mechanistic hypotheses will be presented.

 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

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