Synthetically Useful Wagner-Meerwein Rearrangement of α-Quaternary β-Bromovinyl Methyl Ethers

A synthetically useful Wagner–Meerwein (WM) rearrangement is reported in this paper. The investigation on the design and optimization involved the substrates α‐quaternary β‐bromovinyl methyl ethers as well as the reaction conditions. γ‐Aryl α,β‐unsaturated aldehydes with versatile synthetic uses could readily be obtained through a special pathway in high yields. For example, tricyclic aromatic systems were constructed efficiently through a tandem WM rearrangement/Friedel–Crafts alkylation.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)